Genomes and Genes
Summary: Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)
Publications359 found, 100 shown here
- Extreme bendability of DNA less than 100 base pairs long revealed by single-molecule cyclizationReza Vafabakhsh
Department of Physics, University of Illinois at Urbana Champaign, Urbana, IL 61801, USA
Science 337:1097-101. 2012..We developed a fluorescence-based, protein-free assay for studying the cyclization of single DNA molecules in real time...
- Palladium-catalyzed oxidative carbocyclization/arylation of enallenesTuo Jiang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE 10691, Stockholm, Sweden
Org Lett 13:5838-41. 2011..The reaction shows wide tolerance toward highly functionalized arylboronic acids and results in a cis addition of two carbon moieties to an olefin in good to excellent yields...
- Palladium-catalyzed oxidative diarylating carbocyclization of enynesMin Jiang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE 106 91 Stockholm, Sweden
Org Lett 14:3538-41. 2012..Control experiments suggest that the reaction starts with an arylpalladation of the alkyne, followed by carbocyclization, transmetalation, and reductive elimination to afford the diarylated product...
- Effect of peptide fragment size on the propensity of cyclization in collision-induced dissociation: oligoglycine b(2)-b(8)Xian Chen
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA
J Am Chem Soc 131:18272-82. 2009..This rearrangement mechanism is thought to be due to a head-to-tail cyclization reaction, where the N-terminal and C-terminal part of the fragment are fused into a macrocycle (= cyclic ..
- Cyclization reaction of peptide fragment ions during multistage collisionally activated decomposition: an inducement to lose internal amino-acid residuesChenxi Jia
Chemical Engineering Research Center, School of Chemical Engineering and Technology, Tianjin University, Tianjin, People s Republic of China
J Am Soc Mass Spectrom 18:663-78. 2007..The unique fragmentation consisting of multiple steps is induced by a cyclization reaction of b ions, the mechanism of which has been probed by experiments of N-acetylation, MS(n), rearranged-..
- Bioconjugation with strained alkenes and alkynesMarjoke F Debets
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ, The Netherlands
Acc Chem Res 44:805-15. 2011..In the search for bioorthogonal reactions, cycloadditions of cyclic alkenes and alkynes have now established themselves as powerful tools in reagent-free bioconjugations...
- A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systemsNicholas J Agard
Department of Chemistry, Howard Hughes Medical Institute, University of California, and Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA
J Am Chem Soc 126:15046-7. 2004..The utility of the reaction was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity...
- Rapid and quantitative cyclization of multiple peptide loops onto synthetic scaffolds for structural mimicry of protein surfacesPeter Timmerman
Pepscan Systems B V P O Box 2098, 8203 AB Lelystad, The Netherlands
Chembiochem 6:821-4. 2005
- Structural biology and chemistry of the terpenoid cyclasesDavid W Christianson
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
Chem Rev 106:3412-42. 2006
- Side chain-to-side chain cyclization by click reactionAlexandra Le Chevalier Isaad
Laboratory of Peptide and Protein Chemistry and Biology, Polo Scientifico e Tecnologico, University of Florence, I 50019 Sesto Fiorentino, Italy
J Pept Sci 15:451-4. 2009..Herein, we provide a detailed protocol for the syntheses of model heterodetic cyclopeptides as a prototypical intramolecular CuAAC, using as a model a sequence derived from parathyroid hormone-related protein...
- Cu-free click cycloaddition reactions in chemical biologyJohn C Jewett
Department of Chemistry, University of California, Berkeley, CA 94720, USA
Chem Soc Rev 39:1272-9. 2010..This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions...
- Cyclization of conotoxins to improve their biopharmaceutical propertiesRichard J Clark
The University of Queensland, Institute for Molecular Bioscience, Brisbane, QLD 4072, Australia
Toxicon 59:446-55. 2012..article gives a brief background on conotoxins, describes their structures and highlights methods for synthetic cyclization to improve their biopharmaceutical properties...
- Cyclization and rearrangement reactions of a(n) fragment ions of protonated peptidesBenjamin J Bythell
Computational Proteomics Group, German Cancer Research Center, Im Neuenheimer Feld 580, 69120 Heidelberg, Germany
J Am Chem Soc 132:14766-79. 2010..Overall, theory and infrared spectroscopy provide compelling evidence that a(n) ions undergo cyclization and/or rearrangement reactions, and the resulting structure(s) observed under our experimental conditions ..
- Stabilization of native protein fold by intein-mediated covalent cyclizationNeal K Williams
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia
J Mol Biol 346:1095-108. 2005..coli DnaB helicase was used as a model system to assess the stabilization against unfolding gained by covalent cyclization. Cyclization was achieved in vivo by formation of an amide bond between the N and C termini with the help of a ..
- Chemical modifications designed to improve peptide stability: incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclizationLuca Gentilucci
Department of Chemistry G Ciamician, Universita degli Studi di Bologna, Via Selmi 2, 40126 Bologna, Italy
Curr Pharm Des 16:3185-203. 2010..This review focuses on modified peptides in which the peptide character is still preponderant, with particular emphasis on the chemical methodologies utilized to introduce the modifications...
- Marine molecular machines: heterocyclization in cyanobactin biosynthesisJohn A McIntosh
Department of Medicinal Chemistry, College of Pharmacy, University of Utah, Salt Lake City, UT 84112 USA
Chembiochem 11:1413-21. 2010..The cyanobactin pathway enzymes, PatD and TruD, are thiazoline and oxazoline synthetases...
- Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketonesYe Wei
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore
J Am Chem Soc 134:9098-101. 2012We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant...
- Gold(I)-catalyzed coupling reactions for the synthesis of diverse small molecules using the build/couple/pair strategyTuoping Luo
Howard Hughes Medical Institute, Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA
J Am Chem Soc 131:5667-74. 2009..These pairing reactions include one based on a novel aza-Wittig-6pi-electrocyclization sequence and others based on ring-closing metathesis reactions...
- Mechanism of cyclizing NAD to cyclic ADP-ribose by ADP-ribosyl cyclase and CD38Richard Graeff
Department of Physiology, University of Minnesota, Minneapolis, Minnesota 55455, USA
J Biol Chem 284:27629-36. 2009..This study provides the first detailed evidence of the cyclization process and demonstrates the feasibility of engineering the reactivity of the enzymes by mutation, setting the ..
- Collective synthesis of natural products by means of organocascade catalysisSpencer B Jones
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA
Nature 475:183-8. 2011..The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine...
- Synthesis of polysubstituted imidazo[1,2-a]pyridines via microwave-assisted one-pot cyclization/Suzuki coupling/palladium-catalyzed heteroarylationJamal Koubachi
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Universite d Orleans, BP 6759, 45067 Orleans Cedex 2, France
J Org Chem 72:7650-5. 2007..derivatives using a microwave-assisted one-pot, two-step Suzuki/heteroarylation or one-pot, three-step cyclization/Suzuki/heteroarylation was developed...
- Macrocyclization strategies in polyketide and nonribosomal peptide biosynthesisFlorian Kopp
Fachbereich Chemie Biochemie, Philipps Universitat Marburg, Hans Meerwein Strasse, 35043, Marburg, Germany
Nat Prod Rep 24:735-49. 2007..Further, it is illustrated that macrocyclization is not restricted to secondary metabolites, but represents a commonly found structural motif of other biologically active proteins and peptides...
- Total synthesis of alpha-pyrone meroterpenoids, novel bioactive microbial metabolitesToshiaki Sunazuka
Kitasato Institute for Life Sciences, Kitasato University, and The Kitasato Institute, Shirokane, Minato ku, Japan
Chem Rev 105:4559-80. 2005
- Asymmetric synthesis of isoquinoline alkaloidsMaria Chrzanowska
Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60 780 Poznan, Poland
Chem Rev 104:3341-70. 2004
- On the origins of triterpenoid skeletal diversityRan Xu
Department of Chemistry, Rice University, 6100 S Main Street, Houston, TX 77005, USA
Phytochemistry 65:261-91. 2004..skeletons are known from natural sources or enzymatic reactions that are structurally consistent with being cyclization products of squalene, oxidosqualene, or bis-oxidosqualene...
- Biosynthetic diversity in plant triterpene cyclizationDereth R Phillips
Department of Biochemistry and Cell Biology and Department of Chemistry, Rice University, 6100 Main Street, Houston, TX 77005, USA
Curr Opin Plant Biol 9:305-14. 2006..By contrast, the phylogenetic relationships of cyclases that generate nonsteroidal triterpene alcohols do not consistently reflect their catalytic properties and might indicate recent and rapid catalytic evolution...
- Structural determinants for N1/N7 cyclization of nicotinamide hypoxanthine 5'-dinucleotide (NHD+) derivatives by ADP-ribosyl cyclase from aplysia californica: Ca2+-mobilizing activity of 8-substituted cyclic inosine 5'-diphosphoribose analogues in T-lymphChristelle Moreau
Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom
J Med Chem 49:5162-76. 2006..hypoxanthine 5'-dinucleotide (NHD+) analogues modified at C-8 (2-5) and 7-deaza-NHD+ were synthesized, and cyclization in the presence of Aplysia ADP-ribosyl cyclase was studied...
- Microwave-assisted syntheses of N-heterocycles using alkenone-, alkynone- and aryl-carbonyl O-phenyl oximes: formal synthesis of neocryptolepineFernando Portela-Cubillo
School of Chemistry, EaStCHEM, University of St Andrews, St Andrews, Fife KY16 9ST, UK
J Org Chem 73:5558-65. 2008..However, iminyl radicals did cyclize onto indoles, enabling indolopyridines to be prepared. The latter route was exploited in a short formal synthesis of neocryptolepine starting from 2-((1H-indol-3-yl)methyl)cyclohexanone...
- Antioxidant activity of the anti-inflammatory compound ebselen: a reversible cyclization pathway via selenenic and seleninic acid intermediatesBani Kanta Sarma
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India
Chemistry 14:10603-14. 2008..the concentration of the thiol is relatively low in the reaction mixture, the selenenic acid undergoes a rapid cyclization to produce ebselen...
- Orchestration of discoid polyketide cyclization in the resistomycin pathwayKathrin Fritzsche
Leibniz Institute for Natural Product Research and Infection Biology, HKI, Department of Biomolecular Chemistry, Beutenbergstr 11a, 07745 Jena, Germany
J Am Chem Soc 130:8307-16. 2008..In total three cyclases that are involved in discoid cyclization (RemI, RemF, and RemL) were identified by mutational analyses and in vivo pathway reconstitution...
- Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphatesJoseph P Noel
Howard Hughes Medical Institute, USA
ACS Chem Biol 5:377-92. 2010..originates from the enzyme-catalyzed ionization of (trans,trans)-farnesyl diphosphate (FPP) (1a) and subsequent cyclization along either 2,3-transoid or 2,3-cisoid farnesyl cation pathways...
- Cyclization of hydrazones of 2-acetyl-1-naphthol and 1-acetyl-2-naphthol with triphosgene. Synthesis of Spiro naphthoxazine dimersAbdullah Saad Al-Bogami
Department of Chemistry, King Saud University, P O Box 2455, Riyadh 11451, Saudi Arabia
Molecules 14:2147-59. 2009b>Cyclization of hydrazones derived from 2-acetyl-1-naphthol and 1-acetyl-2-naphthol with triphosgene gave naphtho[1,2-e]-1,3-oxazines, naphtho[2,1-e]-1,3-oxazines or their spiro dimers depending on the molar ratio of triphosgene used for ..
- Spectroscopic, steady-state kinetic, and mechanistic characterization of the radical SAM enzyme QueE, which catalyzes a complex cyclization reaction in the biosynthesis of 7-deazapurinesReid M McCarty
Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, USA
Biochemistry 52:188-98. 2013..These studies implicate 5'-dAdo(•) as the initiator of the ring contraction reaction catalyzed by QueE by abstraction of the H atom from C-6 of CPH(4)...
- Design and synthesis of medium-ring lactam libraries inspired by octalactin a. A convergent-divergent approachNeil Brown
Department of Chemistry, University of Missouri, 205 Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, Missouri 64110, USA
J Comb Chem 10:628-31. 2008
- Structure-activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptidesYaniv Linde
Institute of Chemistry, Safra Campus, Givat Ram, The Hebrew University of Jerusalem, Jerusalem 91904, Israel
Biopolymers 90:671-82. 2008Backbone cyclization (BC) and N-methylation have been shown to enhance the activity and/or selectivity of biologically active peptides and improve metabolic stability and intestinal permeability...
- Total synthesis of the aspercyclidesJiří Pospíšil
Max Planck Institut fur Kohlenforschung, 45470 Mulheim Ruhr, Germany
Chemistry 15:5956-68. 2009..The preparation of the required cyclization precursor 43 hinged on a palladium-catalyzed ortho-iodination reaction of 2-methylbenzoic acid, an efficient ..
- Palladium(II)-catalyzed cyclization of unsaturated hydroperoxides for the synthesis of 1,2-dioxanesJason R Harris
Department of Chemistry, University of California, Irvine, California 92697 2025, USA
Org Lett 11:3290-3. 2009The cyclization of gamma,delta-unsaturated tertiary hydroperoxides in the presence of a palladium(II) catalyst afforded 1,2-dioxanes resembling biologically active natural products...
- Reactivity and regioselectivity in 1,3-dipolar cycloadditions of azides to strained alkynes and alkenes: a computational studyFranziska Schoenebeck
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
J Am Chem Soc 131:8121-33. 2009..Trans-cycloalkene dipolarophiles have much lower barriers than cis-cycloalkenes...
- X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphateEkaterina Y Shishova
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
Biochemistry 46:1941-51. 2007Aristolochene synthase from Aspergillus terreus catalyzes the cyclization of the universal sesquiterpene precursor, farnesyl diphosphate, to form the bicyclic hydrocarbon aristolochene. The 2...
- Chemical synthesis, backbone cyclization and oxidative folding of cystine-knot peptides: promising scaffolds for applications in drug designMichael Reinwarth
Institute for Organic Chemistry and Biochemistry, Technische Universitat Darmstadt, Darmstadt, Germany
Molecules 17:12533-52. 2012..residues), the chemical synthesis route is challenging since it involves critical steps such as head-to-tail cyclization and oxidative folding towards the respective bioactive isomer...
- Tetrasubstituted 2-imidazolones via Ag(I)-catalyzed cycloisomerization of propargylic ureasVsevolod A Peshkov
Laboratory for Organic and Microwave Assisted Chemistry LOMAC, Department of Chemistry, Katholieke Universiteit Leuven, Leuven, Belgium
J Org Chem 76:5867-72. 2011..A one-pot protocol based on a Ag(I)-catalyzed cycloisomerization of propargylic ureas, derived from secondary propargylamines and isocyanates, was developed for the generation of the 2-imidazolone core...
- Effects of cyclization on stability, structure, and activity of α-conotoxin RgIA at the α9α10 nicotinic acetylcholine receptor and GABA(B) receptorReena Halai
Institute for Molecular Bioscience, Division of Chemistry and Structural Biology, The University of Queensland, Brisbane, Queensland 4072, Australia
J Med Chem 54:6984-92. 2011..Here, we improved the biopharmaceutical properties of RgIA by backbone cyclization using 3-7 residue peptidic linkers...
- Reductive cyclization cascades of lactones using SmI2-H2ODixit Parmar
School of Chemistry, University of Manchester, Manchester, United Kingdom
J Am Chem Soc 133:2418-20. 2011Lactones bearing two alkenes or an alkene and an alkyne undergo reductive cyclization cascades upon treatment with SmI(2)-H(2)O, giving decorated azulene motifs in excellent yields with good diastereocontrol.
- Cysteine cyclic pyrrole-imidazole polyamide for sequence-specific recognition in the DNA minor grooveHironobu Morinaga
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606 8502, Japan
J Am Chem Soc 133:18924-30. 2011..Here, we describe a novel cyclization method for producing PI polyamides using cysteine and a chloroacetyl residue...
- Selective transition state stabilization via hyperconjugative and conjugative assistance: stereoelectronic concept for copper-free click chemistryBRIAN GOLD
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306 4390, USA
J Org Chem 77:75-89. 2012..Further computational and experimental studies confirmed the generality of the above accelerating effects and compared them with the conjugative TS stabilization by π-acceptors...
- Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandisKe Zhou
Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University, Ames, Iowa 50011, USA
J Biol Chem 287:6840-50. 2012..for diterpene synthase activity, catalyzing class I (ionization-initiated) and class II (protonation-initiated) cyclization reactions. Reported here is the crystal structure of AgAS at 2...
- Aberrant cyclization affords a C-6 modified cyclic adenosine 5'-diphosphoribose analogue with biological activity in Jurkat T cellsChristelle Moreau
Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom
J Med Chem 55:1478-89. 2012....
- Tandem Rh(III)-catalyzed oxidative acylation of secondary benzamides with aldehydes and intramolecular cyclization: the direct synthesis of 3-hydroxyisoindolin-1-onesSatyasheel Sharma
Department of Chemistry, University of Ulsan, Ulsan, 680 749, Republic of Korea
Org Lett 14:906-9. 2012..between secondary benzamides and aryl aldehydes via sp(2) C-H bond activation followed by an intramolecular cyclization is described...
- A diversity-oriented synthesis approach to macrocycles via oxidative ring expansionFelix Kopp
Molecular Pharmacology and Chemistry Program, Memorial Sloan Kettering Cancer Center, New York, New York, USA
Nat Chem Biol 8:358-65. 2012..Cheminformatic analysis indicates that these macrocycles access regions of chemical space that overlap with natural products, distinct from currently targeted synthetic drugs...
- Identification and characterization of xiamycin A and oxiamycin gene cluster reveals an oxidative cyclization strategy tailoring indolosesquiterpene biosynthesisHuixian Li
CAS Key Laboratory of Marine Bio resources Sustainable Utilization, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China
J Am Chem Soc 134:8996-9005. 2012..Most notably, the flavin dependent oxygenase XiaI was biochemically characterized in vitro to convert indosespene to XMA, revealing an unusual oxidative cyclization strategy tailoring indolosesquiterpene biosynthesis.
- Cyclization of the intrinsically disordered α1S dihydropyridine receptor II-III loop enhances secondary structure and in vitro functionHan Shen Tae
John Curtin School of Medical Research, Australian National University, PO Box 334, Canberra, Australian Capital Territory 2601, Australia
J Biol Chem 286:22589-99. 2011..RyR1) increased 4-fold, and its ability to activate RyR1 channels in lipid bilayers was enhanced 3-fold by cyclization. These functional changes were predicted consequences of the structural enhancement...
- Aza-1,2,3-triazole-3-alanine synthesis via copper-catalyzed 1,3-dipolar cycloaddition on aza-progargylglycineCaroline Proulx
Departement de Chimie, Universite de Montreal, C P 6128, Succursale Centre Ville, Montreal, Quebec H3C 3J7, Canada
J Org Chem 75:5385-7. 2010..Circular dichroism spectroscopy in water demonstrated that azapeptides which possess an aza-1,2,3-triazole-3-alanine residue at the Trp(4) position of the GHRP-6 sequence adopt beta-turn conformations...
- Effect of the His residue on the cyclization of b ionsBenjamin J Bythell
Computational Proteomics Group, German Cancer Research Center DKFZ, Heidelberg, Germany
J Am Soc Mass Spectrom 21:1352-63. 2010..There is compelling experimental and theoretical evidence for formation of nondirect sequence ions via cyclization/reopening chemistry in the CID spectra of the b ions when the His residue is near the C-terminus...
- One-pot cyclization of 2-aminophenethyl alcohols: a novel and direct approach to the synthesis of N-acyl indolinesZengxue Wang
Department of Chemistry, Shanghai University, Shanghai, China
J Org Chem 72:9364-7. 2007A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh3, CCl4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields...
- Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclizationAmy B Dounay
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, California 92697 2025, USA
J Am Chem Soc 130:5368-77. 2008..A cascade catalytic asymmetric Heck-iminium cyclization was developed that rapidly provides 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazoles in high enantiomeric purity...
- Reaction discovery employing macrocycles: transannular cyclizations of macrocyclic bis-lactamsChong Han
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA
Org Lett 11:413-6. 2009..Preliminary mechanistic studies support an olefin isomerization-intramolecular conjugate addition pathway...
- Skeletal diversity via cationic rearrangements of substituted dihydropyransMatthew R Medeiros
Department of Chemistry, Center for Chemical Methodology and Library Development CMLD BU, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA
Org Lett 12:3222-5. 2010..Substituted dihydropyrans, easily accessed from a commercially available glycal, undergo acid-catalyzed rearrangement to provide highly functionalized isochroman and dioxabicyclooctane scaffolds...
- Highly Z- and enantioselective ring-opening/cross-metathesis reactions catalyzed by stereogenic-at-Mo adamantylimido complexesIsmail Ibrahem
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
J Am Chem Soc 131:3844-5. 2009..Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (>or=87:13 Z/E)...
- Improved proteolytic stability of chicken cathelicidin-2 derived peptides by D-amino acid substitutions and cyclizationE Margo Molhoek
TNO Defense, Security and Safety, Rijswijk, The Netherlands
Peptides 32:875-80. 2011..we engineered novel chicken cathelicidin-2 analogs by substitution of l- with D-amino acids and head-to-tail cyclization. Both cyclic and D-amino acid variants showed enhanced stability in human serum compared to C1-15 and F(2,5,12)..
- First determination of the rate constant for ring-closure of an azahexenoyl radical: 6-aza-7-ethyl-5-hexenoylSara H Kyne
ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Australia
Chem Commun (Camb) 46:6521-3. 2010..utilising free radical carbonylation chemistry provide a first estimate for the rate constant for 6-endo cyclization of the 6-aza-7-ethyl-5-hexenoyl radical of (4.8 +/- 2...
- (5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: mechanistic insights on the 2'-deoxyguanosin-5'-yl radical cyclizationChryssostomos Chatgilialoglu
ISOF, Consiglio Nazionale delle Ricerche, Bologna, Italy
Chem Res Toxicol 20:1820-4. 2007..The observed (5'R)/(5'S) ratio of 8:1 was obtained in both sets of experiments. The mechanism of the cyclization reaction is discussed in some detail, and the diastereomeric outcome is rationalized in terms of favorable ..
- Synthesis of novel peptide linkers: simultaneous cyclization and labelingGajanan K Dewkar
Department of Chemistry and Massey Cancer Center, Virginia Commonwealth University, 401 College Street, Richmond, Virginia 23298 0037, USA
Org Lett 11:4708-11. 2009..These reagents can be used to simultaneously cyclize and label peptides containing two cysteines. Many labels are compatible with this method including lipids, fluorescent groups, and biotin...
- Template effects in S(N)2 displacements for the preparation of pseudopeptidic macrocyclesVicente Martí-Centelles
Departament de Quimica Inorganica i Organica, Universitat Jaume I 12071 Castelló, Spain
Chemistry 18:2409-22. 2012..Interestingly, the presence of different substituents on the constituent amino acids seems to play a minor role in the overall process...
- The remarkable metal-catalysed olefin metathesis reactionAmir H Hoveyda
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
Nature 450:243-51. 2007..Nonetheless, the full potential of olefin metathesis will be realized only when additional catalysts are discovered that are truly practical and afford exceptional selectivity for a significantly broader range of reactions...
- A regioselective approach to trisubstituted 2 (or 6)-arylaminopyrimidine-5-carbaldehydes and their application in the synthesis of structurally and electronically unique GlambdaC base precursorsRachel L Beingessner
National Institute for Nanotechnology and Department of Chemistry, University of Alberta, 11421 Saskatchewan Drive, Edmonton, Alberta, T6G 2M9, Canada
J Org Chem 73:931-9. 2008..Furthermore, these fused-bicyclic compounds are readily derivatized using the Suzuki cross-coupling reaction to generate electronically and structurally unique GlambdaC base precursors...
- Synthesis of unique scaffolds via Diels-Alder cycloadditions of tetrasubstituted cyclohexadienesAmanda L Jones
Department of Chemistry and the Center for Chemical Methodology and Library Development CMLD BU, Boston University, Boston, Massachusetts 02215, USA
Org Lett 12:1592-5. 2010..Reactive heterodienophiles, including singlet oxygen ((1)O(2)), 4-substituted-1,2,4-triazoline-3,5-diones (TADs), and aryl- and acylnitroso compounds were employed, yielding novel heterocyclic products...
- Gold(I)-catalyzed regioselective cyclizations of silyl ketene amides and carbamates with alkynesEllen C Minnihan
Department of Medicinal Chemistry, Merck Research Laboratories, Merck and Co Inc, P O Box 2000, Rahway, NJ 07065, USA
J Org Chem 72:6287-9. 2007..The gold(I)-catalyzed regioselective cyclizations of silyl ketene amides or carbamates with alkynes were utilized to construct cyclopentanes or dehydro-delta-lactams...
- Conversion of squalene to the pentacarbocyclic hopeneDirk J Reinert
Institut fur Organische Chemie und Biochemie, Albert Ludwigs Universitat, Albertstr 21, D 79104 Freiburg, Germany
Chem Biol 11:121-6. 2004..The structure analysis revealed a mobile region between the active center cavity and the membrane, which may melt, opening a passage for squalene and hopene...
- Synthesis of (-)-conocarpan by two routes based on radical cyclization and establishment of its absolute configurationDerrick L J Clive
Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
Org Biomol Chem 6:1831-42. 2008..The first (98% ee) is based on formal radical cyclization onto a benzene ring, and involves a 5-exo-trigonal closure onto a double bond restrained within a 6-membered ..
- Synthesis of novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones from Sonogashira products and intramolecular cyclization: Antitumoral activity evaluationMaria João R P Queiroz
Centro de Quimica, Universidade do Minho, Campus de Gualtar, 4710 057 Braga, Portugal
Eur J Med Chem 44:1893-9. 2009..tricyclic lactones) were prepared either by a tandem one-pot Sonogashira coupling and intramolecular cyclization, reacting the 3-bromobenzo[b]thiophene-2-carboxylic acid with arylacetylenes, or by Sonogashira coupling of the ..
- Non-enzymatic cyclization of creatine ethyl ester to creatinineMatthew W Giese
Department of Chemistry, Marian University, Indianapolis, IN 46222, USA
Biochem Biophys Res Commun 388:252-5. 2009..It was found that mild aqueous conditions result in the cyclization of creatine ethyl ester to provide inactive creatinine as the exclusive product, and this transformation ..
- Gold-catalyzed synthesis of carbon-bridged medium-sized ringsFrancis Barabé
Center for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5
Org Lett 11:4236-8. 2009..Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphino gold(I) catalysts...
- Highly efficient Cu(I)-catalyzed synthesis of N-heterocycles through a cyclization-triggered addition of alkynesJunbin Han
Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA
J Am Chem Soc 132:916-7. 2010..An aminoalkyne (terminal or internal) and a terminal alkyne furnish functionalized five-, six-, and seven-membered N-heterocycles in excellent yields via a Cu(I)-catalyzed, one-pot, tandem hydroamination/alkynylation process...
- Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolinesYongxiang Liu
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309, USA
Org Lett 12:1448-51. 2010Two highly stereoselective cationic gold(I)-catalyzed tandem cyclization reactions of alkynylindoles are described. These reactions demonstrated a novel and general strategy to rapidly construct highly functionalized polycyclic indolines...
- Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomersFernando Lopez-Gallego
Department of Biochemistry, University of Minnesota, Paul, MN 55108, USA
Chembiochem 11:1093-106. 2010Sesquiterpene synthases catalyze with different catalytic fidelity the cyclization of farnesyl pyrophosphate (FPP) into hundreds of known compounds with diverse structures and stereochemistries...
- Azaanthraquinone assembly from N-propargylamino quinone via a Au(I)-catalyzed 6-endo-dig cycloisomerizationChunhui Jiang
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P R China
J Org Chem 75:4323-5. 2010..The catalytic process was applied to the synthesis of alkaloid cleistopholine and its analogues. A mechanism involving benign nucleophilicity of the aminoquinone was proposed...
- Genetic interception and structural characterization of thiopeptide cyclization precursors from Bacillus cereusAlbert A Bowers
Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA
J Am Chem Soc 132:12182-4. 2010..These results identify TclM and its homologues in other thiazolyl peptide producing strains as the enzymes responsible for the trans-annular heteroannulation at core of this class of molecules...
- Radiolytic cyclization of stem-and-loop structured oligodeoxynucleotide with neighboring arrangement of α,ω-bis-disulfidesKazuhito Tanabe
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615 8510, Japan
Org Biomol Chem 8:4837-42. 2010..that forms a stem-and-loop structure with a neighboring arrangement of α,ω-bis-disulfides underwent efficient cyclization via an intramolecular exchange reaction at the disulfide moieties with a multiple turnover process...
- Total synthesis and antimicrobial activity of a natural cycloheptapeptide of marine originRajiv Dahiya
Department of Pharmaceutical Chemistry, NRI Institute of Pharmacy, Bhopal 462 021, Madhya Pradesh, India
Mar Drugs 8:2384-94. 2010..Boc-L-Pro-L-Ile-L-Pro-OH tripeptide unit with the L-Phe-L-Pro-L-Pro-L-Tyr-OMe tetrapeptide unit, followed by cyclization of the resulting linear heptapeptide fragment...
- Molecular mechanism of enzymatic allene oxide cyclization in plantsEckhard Hofmann
Biophysics, Department of Biology and Biotechnology, Ruhr University Bochum, Universitaetsstrasse 150, D 44801 Bochum, Germany
Plant Physiol Biochem 46:302-8. 2008..the first oxylipin with signal character, cis-(+)-12-oxo-phytodienoic acid (OPDA), is produced in a cyclization reaction catalyzed by allene oxide cyclase (AOC)...
- Rhodium-catalyzed synthesis of eight-membered ringsBrenton DeBoef
Department of Chemistry, Washington University, One Brookings Drive, Saint Louis, Missouri 63130 4899, USA
J Org Chem 72:799-804. 2007..A catalyst system that provides cyclooctatrienes in greater than 70% yield is reported. Several experiments to determine the nature of the catalyst are described...
- Mutants of the zinc ligands of lacticin 481 synthetase retain dehydration activity but have impaired cyclization activityMoushumi Paul
Department of Chemistry, University of Illinois at Urbana Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
Biochemistry 46:6268-76. 2007..However, these mutations compromised cyclization activity when investigated with full length or truncated peptide substrates...
- Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key stepBart C J van Esseveldt
Radboud University Nijmegen, Institute for Molecules and Materials, Toernooiveld 1, NL 6525 ED Nijmegen, The Netherlands
J Org Chem 70:1791-5. 2005..The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containing amino acids...
- Intein-mediated cyclization of a soluble and a membrane protein in vivo: function and stabilityChristian Siebold
Departement fur Chemie und Biochemie, Universitat Bern, Bern, Switzerland
Biophys Chem 96:163-71. 2002..Cyclized IIA(Glc) displayed increased stability against temperature and GuHCl-induced unfolding (75 vs. 70 degrees C; 1.52 vs. 1.05 M)...
- Extending Pummerer reaction chemistry. development of a strategy for the regio- and stereoselective oxidative cyclization of 3-(omega-nucleophile)-tethered indolesKen S Feldman
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA
J Org Chem 70:6429-40. 2005The brominative cyclization of diastereomeric beta-silyloxy tryptophan derivatives proceeded with divergent regiochemistry (C(2) or C(3) addition), depending on the relative stereochemistry of the silyloxy substituent...
- An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: a powerful and convenient mixed anhydride method promoted by basic catalystsIsamu Shiina
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku ku, Tokyo 162 8601, Japan
J Org Chem 69:1822-30. 2004..The efficiency of the cyclizations is compared to those of other reported lactonizations...
- Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolidesQibin Su
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA
Org Lett 5:2149-52. 2003..Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11...
- Practical solid-phase parallel synthesis of Delta(5)-2-oxopiperazines via N-acyliminium ion cyclizationSung Chan Lee
Department of Chemistry, Seoul National University, Seoul 151 747, Korea
J Comb Chem 9:828-35. 2007A practical solid-phase strategy for the synthesis of Delta(5)-2-oxopiperazines via N-acyliminium ion cyclization has been developed...
- Loading peptidyl-coenzyme A onto peptidyl carrier proteins: a novel approach in characterizing macrocyclization by thioesterase domainsStephan A Sieber
Fachbereich Chemie Biochemie, Philipps Univerität Marburg, Hans Meerwein Strasse, 35032 Marburg, Germany
J Am Chem Soc 125:10862-6. 2003..To explore the great potential of these domains for the catalysis of cell-free cyclization reactions, the new strategy takes advantage of the direct interaction between the natural substrate where the ..
- Second-generation difluorinated cyclooctynes for copper-free click chemistryJulian A Codelli
Departments of Chemistry, University of California, Berkeley, California 94720, USA
J Am Chem Soc 130:11486-93. 2008..These second-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists...
- Effective, selective hydroalkoxylation/cyclization of alkynyl and allenyl alcohols mediated by lanthanide catalystsXianghua Yu
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA
J Am Chem Soc 129:7244-5. 2007
- Elongated multiple electronic cascade and cyclization spacer systems in activatible anticancer prodrugs for enhanced drug releaseF M de Groot
Department of Organic Chemistry, NSR-Center for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
J Org Chem 66:8815-30. 2001..It is expected that the generally applicable novel spacer systems reported herein will contribute to future development of improved enzymatically activated prodrugs...
- Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclizationMarine Boudou
Institut fur Organische Chemie, RWTH Aachen, Landoltweg 1, D 52074 Aachen, Germany
J Org Chem 70:9486-94. 2005..The Pummerer cyclization led to the formation of (S)-(-)-2 with slight racemization (ee = 89%), whereas the Friedel-Crafts reaction ..
- Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalystMasanobu Uchiyama
Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba ku, Sendai 980 8578, Japan
Org Lett 8:5517-20. 2006..investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds...
- Unnatural natural products from the transannular cyclization of lathyrane diterpenesG Appendino
Universita del Piemonte Orientale, DiSCAFF, Viale Ferrucci 33, 28100 Novara, Italy
Org Lett 3:1609-12. 2001..Apparently, Nature is far from having fully exploited the built-in reactivity of these compounds to generate chemical diversity...
- HPLC-MS characterization of cyclo-statherin Q-37, a specific cyclization product of human salivary statherin generated by transglutaminase 2Tiziana Cabras
Department of Sciences Applied to Biosystems, Cagliari University, Monserrato Campus, Monserrato, CA, Italy
J Sep Sci 29:2600-8. 2006..Y, monitored by HPLC-electrospray ionization-ion trap-mass spectrometric analysis, demonstrated that cyclization involved almost specifically Gln-37 (> 95%), with the percentage of Gln-39 implicated in the cross-linkiing ..
- Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitorsManjinder S Lall
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2
J Org Chem 67:1536-47. 2002....
- Scope and mechanistic study of the ruthenium-catalyzed ortho-C-H bond activation and cyclization reactions of arylamines with terminal alkynesChae S Yi
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53201 1881, USA
J Am Chem Soc 127:17000-6. 2005..A mechanism involving rate-determining ortho-C-H bond activation and intramolecular C-N bond formation steps via an unsaturated cationic ruthenium acetylide complex has been proposed...
- Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanonesM Sanchez-Gonzalez
Division of Medicinal and Natural Products Chemistry, Center for Biocatalysis and Bioprocessing, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, USA
J Nat Prod 67:553-8. 2004..flavanones and to O-demethylated and hydroxylated chalcones, some of which functioned as intermediates in the cyclization process...
- Efficient macrocyclization of U-turn preorganized peptidomimetics: the role of intramolecular H-bond and solvophobic effectsJorge Becerril
Department of Inorganic and Organic Chemistry, University Jaume, I E 12080 Castellón, Spain
J Am Chem Soc 125:6677-86. 2003..The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed ..
- Quantitative analysis, using MALDI-TOF mass spectrometry, of the N-terminal hydrolysis and cyclization reactions of the activation process of onconaseMarc Ribo
Laboratori d Enginyeria de Proteïnes, Departament de Biologia, Facultat de Ciencies, Universitat de Girona, Girona, Spain
Eur J Biochem 271:1163-71. 2004..0. The intramolecular cyclization of glutaminyl that renders the pyroglutamyl residue is not accelerated by increasing the concentration of ..
- Analogs of GTP as novel inhibitors of bacterial c-di-GMP-synthesizing enzymesGeorge E Wright; Fiscal Year: 2010..chromatography, and characterized by NMR and LCMS methods;2, test GTP analogs for their ability to inhibit cyclization of GTP to c-di- GMP by the Pseudomonas aeruginosa DGC "PA3702";a coupled assay measuring pyrophosphate release ..
- Synthesis of Medicinally Important HeterocyclesRICHARD LAROCK; Fiscal Year: 2007The vast majority of medicinally important drugs contain a heterocyclic or carbocyclic ring. The electrophilic cyclization of functionally-substituted alkynes has been little studied, although it would appear to be a very promising route ..
- REACTIVITY MODELS FOR ISOPENICILLIN N SYNTHETASEPATRICIA SHAPLEY; Fiscal Year: 1992..biosynthesis of both penicillins and cephalosporins, a small, soluble enzyme is responsible for the oxidative cyclization of the tripeptide delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine to isopenicillin N...
- DNA Topology In TBP/DNA Complexes: Chromatin ConnectionsJason Kahn; Fiscal Year: 2004..to Pol II transcription initiation as part of the TFIID assembly, induces negative supercoiling upon DNA cyclization of short restriction fragments to give minicircies...
- TERPENE CYCLASES: FUNCTIONAL DOMAINS AND STRUCTURESJOSEPH NOEL; Fiscal Year: 2003The objective of this proposal is to understand the structural and mechanistic features governing the cyclization of farnesyl diphosphate (FPP) catalyzed by a homologous set of four plant sesquiterpene cyclases including Nictotiana ..
- FUNGAL POLYKETIDE SYNTHASESCHARLES SIH; Fiscal Year: 2001..to catalyze the assembly of two distinct products with different carbon chain lengths, functionalization and cyclization patterns...
- MANGANESE (III) BASED OXIDATIVE FREE RADICAL CYCLIZATIONBARRY SNIDER; Fiscal Year: 2000..The goal of this research is to develop oxidative free- radical cyclization into a reliable and versatile method for the synthesis of highly functionalized cyclic and polycyclic compounds...
- CD38/ADP RIBOSYL CYCLASE R0LE IN OSTEOCLAST REGULATIONMone Zaidi; Fiscal Year: 2003..The latter is formed from NAD+ following its cyclization by the enzyme, CD38 (an ADP-ribosyl cyclase)...
- Tetrahydrofurans, Tetrahydropyrans and 2H-FuranonesCHRISTOPHER SPILLING; Fiscal Year: 2009..Since the palladium catalyzed cyclization is stereospecific, the stereochemistry of the phosphono allylic carbonates dictates the stereochemistry of new ..
- A Bacitracin derivative for systemic useAke Elhammer; Fiscal Year: 2007..The CES approach combines automated solid-phase peptide synthesis of linear precursor peptides, with enzymatic cyclization using a recombinant thioesterase (TE) domain derived from the relevant Non Ribosomal Peptide Synthetase (NRPS) ..