- Structure of an acidic polysaccharide from the marine bacterium Pseudoalteromonas flavipulchra NCIMB 2033(T)
Department of Chemistry, National University of Ireland, University Road, Galway, Ireland
Carbohydr Res 338:459-62. 2003
- NMR study of virenose and dihydrohydroxystreptose isolated from Coxiella burnetii phase I lipopolysaccharide
Institute of Virology, Slovak Academy of Sciences, Bratislava, Slovak Republic
Carbohydr Res 306:291-6. 1998
..Radziejewska-Lebrecht, and H. Mayer, Eur. J. Biochem., 148 (1985) 455-461] to be present in LPS I in a furanose form, and it appears that a furanose to pyranose tautomerization took place in the course of the isolation procedure...
- Inhibition of glycosaminoglycan synthesis and protein glycosylation with WAS-406 and azaserine result in reduced islet amyloid formation in vitro
Rebecca L Hull
Division of Metabolism, Endocrinology, and Nutrition, Veterans Affairs Puget Sound Health Care System and University of Washington, Seattle, Washington 98108, USA
Am J Physiol Cell Physiol 293:C1586-93. 2007
- The structure of the O-polysaccharide from the lipopolysaccharide of Providencia alcalifaciens O36 containing 3-deoxy-d-manno-oct-2-ulosonic acid
Nina A Kocharova
N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
Carbohydr Res 342:665-70. 2007
..structure: see text]..
- Biosynthesis of the dideoxysugar component of jadomycin B: genes in the jad cluster of Streptomyces venezuelae ISP5230 for L-digitoxose assembly and transfer to the angucycline aglycone
Department of Biology, Dalhousie University, Halifax, Nova Scotia, Canada
Microbiology 148:1091-103. 2002
..The deduced amino acid sequence of a 612 bp ORF (jadR*) downstream of the dideoxysugar biosynthesis genes resembles many TetR-family transcriptional regulator sequences...
- Nucleotide deoxysugars: essential tools for the glycosylation engineering of novel bioactive compounds
Department of Biotechnology Biomaterial Sciences, Helmholtz Institute for Biomedical Engineering, RWTH Aachen University, Worringer Weg 1, D 52056 Aachen, Germany
Curr Med Chem 12:1637-75. 2005
- Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
Carbohydr Res 342:16-22. 2007
..A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide...
- Unusual addition of amines to C-2 of vinyl sulfone-modified-beta-D-pent-2-enofuranosyl carbohydrates: synthesis of a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides
Department of Chemistry, Indian Institute of Technology, Kharagpur, India
Carbohydr Res 343:1287-96. 2008
..Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides...
- Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides
Xiang Bao Meng
Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China
Carbohydr Res 342:1169-74. 2007
..Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS)...
- Alteration of O-specific polysaccharide structure of symbiotically defective Mesorhizobium loti mutant 2213.1 derived from strain NZP2213
Department of General Microbiology, Maria Curie Sklodowska University, Lublin, Poland
Acta Biochim Pol 55:191-9. 2008
..Western immunoblot assay of alkaline de-O-acetylated lipophilic M. loti NZP2213 LPS showed no reactivity with homologous serum indicating a role of O-acetyl groups in its O-specificity...
- Discovery and molecular engineering of sugar-containing natural product biosynthetic pathways in actinomycetes
Tae Jin Oh
Institute of Biomolecule Reconstruction, Department of Pharmaceutical Engineering, SunMoon University, Asan 336 708, Korea
J Microbiol Biotechnol 17:1909-21. 2007
..These recent developments in the engineering of deoxysugars biosynthesis may pave the way to create novel secondary metabolites with potential biological activities...
- Enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose using GerB (dTDP-4-keto-6-deoxy-D-glucose aminotransferase)
Young Soo Chung
Genechem Inc, 59 5 Jang Dong, Yuseong Gu, Daejeon 305 343, South Korea
Carbohydr Res 342:1412-8. 2007
..After purification by two successive preparative HPLC systems, the final product was identified by HPLC and then analyzed by (1)H, (13)C, (1)H-(1)H COSY NMR spectrometry...
- Chemical clockwise tridifferentiation of alpha- and beta-cyclodextrins: bascule-bridge or deoxy-sugars strategies
Universite Pierre et Marie Curie Paris 6, Institut de Chimie Moleculaire FR 2769, Laboratoire de Chimie Organique UMR CNRS 7611, 4 place Jussieu, Paris, France
Chemistry 13:9757-74. 2007
..Bascule-bridge or deoxy-sugars are two complementary means to operate steric decompression and induce selective reactions to efficiently access a number of new patterns of functionalities on concave molecules...
- Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine
E Sethe Burgie
Department of Biochemistry, University of Wisconsin, Madison, Wisconsin 53706, USA
Biochemistry 46:8999-9006. 2007
..Indeed, the nearly 180 degrees difference in hexose orientation explains the equatorial versus axial amino transfer exhibited by DesI and PseC, respectively...
- The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties
Departamento de Biologia Funcional e Instituto Universitario de Oncologia del Principado de Asturias, Universidad de Oviedo, Spain
Mol Gen Genet 264:827-35. 2001
..A pathway is proposed for the biosynthesis of the three sugar moieties in mithramycin...
- Insights about the biosynthesis of the avermectin deoxysugar L-oleandrose through heterologous expression of Streptomyces avermitilis deoxysugar genes in Streptomyces lividans
School of Pharmacy, University of Wisconsin, Madison, WI 53706, USA
Chem Biol 8:681-700. 2001
..The AvrF protein is therefore a 5-epimerase and not a 3,5-epimerase. The ability of the AvrB (mono-)glycosyltransferase to accommodate different deoxysugar intermediates is evident from the structures of the novel avermectins produced...
- Structure of a colitose-containing O-specific polysaccharide of the marine bacterium Pseudoalteromonas tetraodonis IAM 14160(T)
Department of Chemistry, National University of Ireland, Galway, Ireland
Carbohydr Res 333:41-6. 2001
- A diastereoselective and general route to 5-amino-5-deoxysugars: influence of C-3 substitution on the addition of amines to C-5 of vinyl sulfone-modified hex-5-enofuranosyl carbohydrates
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India
J Org Chem 70:8047-54. 2005
..The selectivity is lost when an allo derivative with OBn at the alpha-face of C-3 is used. Selected products were desulfonated to establish this new approach as a general and versatile strategy for accessing 5-amino-5-deoxysugars...
- Synthesis of N-acylated 7-amino-2,6,7-trideoxy-D-erythroheptopyranosides from methyl alpha-D-mannoside
Institut fur Pharmazeutische und Medizinische Chemie der Westfalischen Wilhelms Universitat Munster, Hittorfstrasse 58 62, D 48149 Munster, Germany
Carbohydr Res 340:2483-93. 2005
..Nucleophilic substitution of 15 with KCN, subsequent hydrogenation with H2/Raney Ni and acylation with various carboxylic acid derivatives yielded 7-(acylamino)heptopyranosides 19-22...
- Engineering deoxysugar biosynthetic pathways from antibiotic-producing microorganisms. A tool to produce novel glycosylated bioactive compounds
Departamento de Biologia Funcional e Instituto Universitario de Oncologia del Principado de Asturias, Universidad de Oviedo, 33006, Oviedo, Spain
Chem Biol 9:721-9. 2002
..The system was also used to generate an L-rhamnosyl derivative (through a two-gene deletion) and an L-rhodinosyl derivative (through a combination of a gene replacement and a gene addition)...
- Elucidation of the O-chain structure from the lipopolysaccharide of Agrobacterium tumefaciens strain C58
Cristina De Castro
Dipartimento di Chimica Organica e Biochimica, Universita di Napoli Federico II, Via Cintia 4, 80126 Napoli, Italy
Carbohydr Res 338:1891-4. 2003
..This structure, determined by spectroscopical and chemical methods, is strictly correlated to that of Rhizobium loti strain NZP2213, which differs for the degree and the position of O-acetylation...
- Efficient route to 2-deoxy beta-O-aryl-d-glycosides via direct displacement of glycosyl iodides
Son N Lam
Department of Chemistry, University of California, Davis, One Shields Ave, Davis, California 95616, USA
Org Lett 5:4219-22. 2003
..The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence...
- Structural and serological studies on a new 4-deoxy-d-arabino-hexose-containing O-specific polysaccharide from the lipopolysaccharide of Citrobacter braakii PCM 1531 (serogroup O6)
L Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland
Eur J Biochem 270:2732-8. 2003
- Creation of the first anomeric D/L-sugar kinase by means of directed evolution
Laboratory for Biosynthetic Chemistry, Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA
Proc Natl Acad Sci U S A 100:13184-9. 2003
- Synthesis of 2,3- or 1,2-unsaturated derivatives of 2-deoxy-2-trifluoromethylhexopyranoses
FB Chemie, Organische Chemie, Universitat Rostock, Albert Einstein Strasse 3a, D 18059 Rostock, Germany
Carbohydr Res 339:1833-7. 2004
..X-ray analyses are given for 1,3,4,6-tetra-O-acetyl-2-chlorodifluoromethyl-2-deoxy-alpha-D-mannopyranose and 4,6-di-O-acetyl-2,3-dideoxy-2-trifluoromethyl-alpha-D-erythro-hex-2-enopyranose...
- Synthesis of the heteropolysaccharide O antigen of Escherichia coli O52 requires an ABC transporter: structural and genetic evidence
TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin Biochip Technology Corporation, Tianjin, People s Republic of China
J Bacteriol 186:4510-9. 2004
..This is the first report of an ABC transporter being involved in translocation of a heteropolysaccharide O antigen in E. coli. Genes specific for E. coli O52 were also identified...
- Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region
Olga V Bystrova
ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
Carbohydr Res 338:1895-905. 2003
..The core was found to be randomly O-acetylated, most O-acetyl groups being located on the terminal rhamnose residue of the outer core region...
- Guanosine diphosphate-4-keto-6-deoxy-d-mannose reductase in the pathway for the synthesis of GDP-6-deoxy-d-talose in Actinobacillus actinomycetemcomitans
Department of Preventive Dentistry, Kyushu University Faculty of Dental Science, Fukuoka, Japan
Eur J Biochem 269:5963-71. 2002
..This paper is the first report on the GDP-6-deoxy-d-talose biosynthetic pathway and the role of GDP-4-keto-6-deoxy-d-mannose reductase in the synthesis of GDP-6-deoxy-d-talose...
- Synthesis of 4-deoxy-L-(and D-)hexoses from chiral noncarbohydrate building blocks
Dipartimento di Chimica Organica e Biochimica, Universita di Napoli Federico II, Via Cynthia, 4 80126 Naples, Italy
J Org Chem 69:7033-7. 2004
..The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers...
- Structure of the O-polysaccharide of Aeromonas hydrophila O:34; a case of random O-acetylation of 6-deoxy-L-talose
Yuriy A Knirel
N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow 119991, Russia
Carbohydr Res 337:1381-6. 2002
- Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides
Dipartimento di Chimica Organica e Biochimica Complesso, Universitario Monte Sant Angelo, Via Cintia 4, 80126, Napoli, Italy
J Am Chem Soc 127:2414-6. 2005
..This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP)...
- LanGT2 Catalyzes the First Glycosylation Step during landomycin A biosynthesis
Albert Ludwigs Universitat, Institut für Pharmazeutische Wissenschaften, Stefan Meier Strasse 19, 79104 Freiburg, Germany
Chembiochem 6:1406-10. 2005
..Heterologous expression of urdGT2 from S. fradiae Tü2717 in this mutant resulted in the production of a novel C-glycosylated angucycline (6)...
- In vitro antiviral activity of some uridine derivatives of 2-deoxy sugars against classical swine fever virus
Department of Molecular Virology, Intercollegiate Faculty of Biotechnology, University of Gdansk and Medical University of Gdansk, Gdansk, Poland
Antiviral Res 86:154-62. 2010
..In our study we tested two of newly designed uridine derivatives of 2-deoxy sugars, IW3 and IW7 mimicking part of tunicamycin...
- Chemical structure and biological significance of lipopolysaccharide from Legionella
Department of Genetics and Microbiology, Maria Curie Skłodowska University, Lublin, Poland
Recent Pat Antiinfect Drug Discov 4:96-107. 2009
..The outer region of the core enriched with 6-deoxy sugars and N- and O- acetylated sugars as well as the highly N- and O-acylated O-chain contribute to a high ..
- Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthe
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 7061, USA
J Am Chem Soc 126:8232-6. 2004
- Phylogenetic analysis of antibiotic glycosyltransferases
Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P R China
J Mol Evol 64:342-53. 2007
..Finally, the evolutionary origins of AGts that do not fall into GT Family 1 are discussed, suggesting that their ancestral proteins appear to be derived from various proteins responsible for primary metabolism...
- Structural studies of the O-antigens of Yersinia pseudotuberculosis O:2a and mutants thereof with impaired 6-deoxy-D-manno-heptose biosynthesis pathway
Anna N Kondakova
ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Carbohydr Res 343:1383-9. 2008
..structure of the long- and short-chain O-antigen of Yersinia pseudotuberculosis O:2a containing two uncommon deoxy sugars, abequose and 6-deoxy-d-manno-heptose (6dmanHep), was established, for the first time, by sugar analysis, NMR ..
- Selective pivaloylation of 2-acetamido-2-deoxy sugars
Department of Radioimmunology, Institute of Immunology, Zagreb, Yugoslavia
Carbohydr Res 182:197-205. 1988
..Methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-alpha- and -beta-D-glucopyranosides and 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-D-glucopyranose were hydrolysed by rabbit serum esterases...
- Sodium-dependent reorganization of the sugar-binding site of SGLT1
Bruce A Hirayama
Department of Physiology, The David Geffen School of Medicine at UCLA, 10833 Le Conte Avenue, Los Angeles, California 90095 1751, USA
Biochemistry 46:13391-406. 2007
..between mutated residues and hydroxyls on the pyranose ring was assessed by comparing the affinities of deoxy sugars to those of glucose...
- Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi
Marilyn G Wiebe
VTT Technical Research Centre of Finland, P, O, Box 1000, FI 02044 VTT, Finland
BMC Biotechnol 10:63. 2010
..The keto-deoxy sugars have been found to be useful precursors for producing further derivatives...
- Structure of the O-antigen of Yersinia pseudotuberculosis O:4b
Anna N Kondakova
N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Carbohydr Res 344:152-4. 2009
The structure of the long-chain O-antigen of Yersinia pseudotuberculosis O:4b containing two uncommon deoxy sugars, tyvelose (3,6-dideoxy-d-arabino-hexose, Tyv) and 6-deoxy-d-manno-heptose (D-6dmanHep), was established by 1D and 2D NMR ..
- Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Carbohydr Res 339:2197-204. 2004
..Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and alpha-anomeric 2-deoxy glycosides were obtained exclusively...
- 11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a Streptomyces cyanogenus K62 mutant strain
Khaled A Shaaban
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536 0596, USA
J Antibiot (Tokyo) 64:141-50. 2011
..11-deoxylandomycinone (IC(50) 2.1 ± 0.3 and 1.2 ± 0.4 μM) and landomycin Y (IC(50) 1.0 ± 0.1 and 2.0 ± 0.1 μM) showed the highest cytotoxic potencies against both the cell lines...
- A new route to dTDP-6-deoxy-l-talose and dTDP-L-rhamnose: dTDP-L-rhamnose 4-epimerase in Burkholderia thailandensis
Hye Gyeong Yoo
Department of Biological Science, Division of Bioscience and Bioinformatics, Myongji University, Yongin 449 728, Republic of Korea
Bioorg Med Chem Lett 21:3914-7. 2011
..WbiB(Bth) alone produced dTDP-Rha when incubated with dTDP-6dTal. This is the first report to demonstrate epimerase activity interconverting between dTDP-Rha and dTDP-6dTal...
- Structure of the major O-specific polysaccharide from the lipopolysaccharide of Pseudomonas fluorescens BIM B-582: identification of 4-deoxy-D-xylo-hexose as a component of bacterial polysaccharides
Olga A Valueva
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
J Nat Prod 74:2161-7. 2011
..In addition, a minor polysaccharide was isolated from the same lipopolysaccharide and found to contain 4-O-methylrhamnose...
- Mechanisms and structures of vitamin B(6)-dependent enzymes involved in deoxy sugar biosynthesis
Anthony J Romo
Division of Medicinal Chemistry, College of Pharmacy, Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA
Biochim Biophys Acta 1814:1534-47. 2011
..This article is part of a Special Issue entitled: Pyridoxal Phosphate Enzymology...
- De novo synthesis of L-colitose and L-rhodinose building blocks
Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476 Potsdam, Germany
J Org Chem 77:870-7. 2012
..Oxidation of this common intermediate finally resulted in the synthesis of the three monosaccharide building blocks...
- Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide
Fabien P Boulineau
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907 2084, USA
J Org Chem 69:3391-9. 2004
..This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues...
- Structural studies of AntD: an N-Acyltransferase involved in the biosynthesis of D-Anthrose
Rachel L Kubiak
Department of Biochemistry, University of Wisconsin, Madison, Wisconsin 53706, United States
Biochemistry 51:867-78. 2012
..Taken together, these data suggest that Asp 94 is important for substrate binding, but probably does not function as an enzymatic base, and that Ser 84 most likely plays a role in the formation of an oxyanion hole...
- Structure-based phylogeny of polyene macrolide antibiotic glycosyltransferases
School of Basic Medical Science, Tianjin Medical University, Tianjin 300070, China
Gene 499:288-96. 2012
..Using structure-based phylogenetic approaches, this study further supported that PEM AGts were the result of HGT between prokaryotes and eukaryotes...
- The synthesis of 2-deoxy-α-D-glycosides from D-glycals catalyzed by TMSI and PPh3
Xi Kai Cui
The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, PR China
Carbohydr Res 358:19-22. 2012
..2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to D-glucal and D-galactal catalyzed by TMSI and PPh(3). The acid labile isopropylidene group is tolerated under this condition...
- Conformational analysis of sulfur-containing 6-deoxy-l-hexose derivatives by molecular modeling and NMR spectroscopy. A theoretical study and experimental evidence of intramolecular nonbonded interactions between sulfur and oxygen
Departamento de Quimica, Centro de Investigacion y de Estudios Avanzados del Instituto Politecnico Nacional, Apartado 14 740, Mexico City 07000, Mexico
J Org Chem 68:7167-75. 2003
..Compounds 9-12 were formed by a molecular rearrangement via sulfonium ion intermediates followed by stereoselective intramolecular cyclizations as formulated by the quantum chemical calculations performed in the present study...
- Synthesis of disaccharides containing 6-deoxy-α-L-talose as potential heparan sulfate mimetics
Jon K Fairweather
Drug Design Group, Progen Pharmaceuticals Ltd, Brisbane Qld 4076, Australia
Molecules 17:9790-802. 2012
..However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics...
- Structure of a colitose-containing O-polysaccharide from the lipopolysaccharide of Providencia alcalifaciens O6
Olga G Ovchinnikova
N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
Carbohydr Res 342:2144-8. 2007
- Differences in the substrate specificity of glycosyltransferases involved in landomycins A and E biosynthesis
Institut für Pharmazeutische Wissenschaften, Albert Ludwigs Universitat, Freiburg, Germany
Appl Microbiol Biotechnol 83:1067-76. 2009
..A producer Streptomyces cyanogenus S136 was constructed, leading to the production of landomycin D with two deoxy sugars in the side chain and proving that LanGT4 is responsible for attaching the third deoxy sugar of the ..
- Synthesis of 2-deoxy-D-arabino/lyxo-hexopyranosyl disaccharides
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Carbohydr Res 343:453-61. 2008
..The activated 2-deoxy-1-thioglycosides served as the common precursors to prepare the 2-deoxy disaccharides with the above configurations...
- A reagent-controlled SN2-glycosylation for the direct synthesis of β-linked 2-deoxy-sugars
John Paul Issa
Department of Chemistry, Tufts University, 62 Talbot Avenue, Medford, Massachusetts 02155, United States
J Am Chem Soc 136:5740-4. 2014
..This approach demonstrates that use of promoters that activate hemiacetals as well-defined intermediates can be used to permit stereoselective glycosylation through an SN2-pathway. ..
- Deoxy sugars: occurrence and synthesis
Rosa M de Lederkremer
CIHIDECAR, Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Adv Carbohydr Chem Biochem 61:143-216. 2007
- Synthesis of carbohydrate-based vinyl selenides via Wittig-type reactions
Departament de Quimica Analitica i Quimica Organica, Facultat de Quimica, Universitat Rovira i Virgili, c o Marcel lí Domingo s n, E 43007 Tarragona, Spain
Carbohydr Res 342:736-43. 2007
..A detailed study of the olefination reaction and the behaviour of vinyl selenides towards the electrophilic-induced cyclization will be discussed...
- [Isolation and characterization of lectin from the surface of Grifola frondosa (FR.) S.F. Gray mycelium]
L V Stepanova
Mikrobiologiia 76:488-93. 2007
..D-glucose and D-glucosamine were detected in the carbohydrate part...
- The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of omega-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides
Anna W Pierwocha
Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44 100 Gliwice, Poland
Carbohydr Res 343:2680-6. 2008
..The second step involves reacting the appropriate glycoside with methylamine...
- De novo asymmetric synthesis and biological evaluation of the trisaccharide portion of PI-080 and vineomycin B2
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA
Org Lett 10:4529-32. 2008
..Significant apoptotic antitumor activity was found for this trisaccharide, which has implication for vineomycin B2 and PI-080 structure-activity relationship...
- Mycobacterium avium glycopeptidolipids require specific acetylation and methylation patterns for signaling through toll-like receptor 2
Department of Biological Sciences, Eck Center for Global Health and Infectious Disease, University of Notre Dame, Indiana 46556, USA
J Biol Chem 283:33221-31. 2008
..These experiments illustrate how subtle changes in a complex TLR2 ligand can alter its affinity for this important receptor, and suggest that M. avium could potentially modify its GPL structure to limit its interaction with TLR2...
- Modulation of deoxysugar transfer by the elloramycin glycosyltransferase ElmGT through site-directed mutagenesis
Departamento de Biología Funcional e Instituto Universitario de Oncología del Principado de Asturias IUOPA, Universidad de Oviedo, 33006 Oviedo, Spain
J Bacteriol 191:2871-5. 2009
- Nucleophilic addition to 2,3-disubstituted butanal derivatives and their application to natural product synthesis
Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Chiba 274 8510, Japan
Chem Pharm Bull (Tokyo) 58:1411-8. 2010
..After separation of this mixture, (±)-34 and (±)-35 were separately converted to (±)-oliose (5) and (±)-boivinose (6), respectively...
- Glycosylation engineering of spinosyn analogues containing an L-olivose moiety
Biotica Technology Ltd, Chesterford Research Park, Cambridge, UK CB10 1XL
Org Biomol Chem 7:1705-8. 2009
..Co-expression of the spinosyn glycosyl transferase SpnP in the resulting mutant endowed upon it the ability to biotransform exogenously added spinosyn aglycones to yield novel spinosyn analogues...
- Structure of a novel α-glucan substitute with the rare 6-deoxy-D-altrose from Lactarius lividatus (mushroom)
Department of Subtropical Bioscience and Biotechnology, University of the Ryukyus, Nishiara, Okinawa 903 0213, Japan
Carbohydr Polym 92:2135-40. 2013
- Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines
Hong Min Liu
Department of Chemistry, Zhengzhou University, Zhengzhou 450052, P R China
Org Biomol Chem 1:1641-2. 2003
- X-ray analysis of D-xylose isomerase at 1.9 A: native enzyme in complex with substrate and with a mechanism-designed inactivator
H L Carrell
Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, PA 19111
Proc Natl Acad Sci U S A 86:4440-4. 1989
..A water molecule binds to C1O and C2O of the substrate and so may act as a proton donor or acceptor in the enolization of a ring-opened substrate...
- Lack of antifertility properties of novel halogenated glycolytic inhibitors and the urinary excretion and metabolism of 1,6-dichloro-1,6-dideoxy-D-fructofuranose in the male rat
A R Jones
School of Molecular and Microbial Biosciences, Discipline of Biochemistry, University of Sydney, Sydney, NSW, Australia
Int J Androl 25:168-74. 2002
..By 24 h little DCF remained and the major metabolite (70%) was BCLA and 20% Cl-. The high rate of dechlorination is most likely responsible for the low antifertility action of DCF...
- [Determination of the D- and L-configurations of amino deoxy sugars by (S)-TBMB carboxylic acid, a fluorescent chiral derivatization reagent]
Department of Biochemistry, School of Life Sciences, Fudan University, Shanghai 200433, China
Sheng Wu Hua Xue Yu Sheng Wu Wu Li Xue Bao (Shanghai) 34:615-8. 2002
..Furthermore, a simple and highly sensitive method for the determination of the D-, L- configuration of amino deoxy sugars was developed based on the same fluorescent labeling method and reverse phase HPLC...
- 2-Deoxy-D-glucose accumulation in adipocytes: apparent transport discrimination between 2-deoxy-D-glucose and 3-O-methyl-D-glucose
K A Thompson
Department of Physiology, University of Pennsylvania, Philadelphia 19104
Biochim Biophys Acta 1011:58-60. 1989
..The results are discussed in light of hypotheses advanced to explain free 2-deoxy-D-glucose accumulation in a variety of cells...
- Synthesis, the crystal structure, and high-resolution NMR spectroscopy of methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-alpha-D-arabino-hexopyranoside
Department of Chemistry, University of Gdansk, 18 19 Sobieski Strasse, PL 80 952 Gdansk, Poland
Carbohydr Res 337:175-81. 2002
..This compound adopts the 4C(1) conformation...
- First preparation of spacer-linked cyclic neooligoaminodeoxysaccharides
Guang Wu Chen
Institut für Organische Chemie Technische Universität Clausthal, Leibnizstrasse 6 38678 Clausthal Zellerfeld, Germany
Chemistry 8:2717-29. 2002
..The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions...
- Formation of unusual sugars: mechanistic studies and biosynthetic applications
Xuemei M He
Division of Medicinal Chemistry, College of Pharmacy, and Department of Chemistry and Biochemistry, University of Texas, Austin, Texas 78712, USA
Annu Rev Biochem 71:701-54. 2002
..This represents a significant progress toward our goal of searching for more potent agents against infectious diseases and malignant tumors...
- Structural analysis of the exopolysaccharide from Burkholderia caribensis strain MWAP71
, , B.P.53, F-38041, Grenoble, France
Carbohydr Res 334:127-33. 2001
- Separation of 6-deoxy-heptan [correction of 6-deoxy-heptane] from a smooth-type lipopolysaccharide preparation of Burkholderia pseudomallei
Department of Bacteriology, The Kitasato Institute, Tokyo, Japan
FEMS Microbiol Lett 199:21-5. 2001
..The 6-deoxy-heptan [corrected] showed no macrophage activation, indicating that this polysaccharide was not the LPS, but one of the capsular polysaccharides of B. pseudomallei...
- Mechanistic studies of the biosynthesis of 3,6-dideoxyhexoses in Yersinia pseudotuberculosis. Purification and stereochemical analysis of CDP-D-glucose oxidoreductase
Department of Chemistry, University of Minnesota, Minneapolis 55455
J Biol Chem 267:5868-75. 1992
..Such a mechanistic and stereochemical convergency found for all sugar oxidoreductases so far characterized suggests the presence of a common progenitor of this class of enzyme...
- Cloning and functional expression of a novel GDP-6-deoxy-D-talose synthetase from Actinobacillus actinomycetemcomitans
Department of Bacteriology and Immunology, Haartman Institute and Biomedicum, PO Box 63, FIN 00014 University of Helsinki, Helsinki, Finland
Glycobiology 13:295-303. 2003
..The functional expression of gts provides another enzymatically defined pathway for the synthesis of GDP-deoxyhexoses, which can be used as donors for the corresponding glycosyltransferases...
- L-Rhamnulose 1-phosphate aldolase of Escherichia coli. The role of metal in enzyme structure
N B Schwartz
Biochemistry 13:1726-30. 1974
- A complete gene cluster from Streptomyces nanchangensis NS3226 encoding biosynthesis of the polyether ionophore nanchangmycin
Bio X Life Science Research Center, Shanghai Jiaotong University, Shanghai 200030, China
Chem Biol 10:431-41. 2003
..In-frame deletion of a KR6 domain generated the nanchangmycin aglycone with loss of 4-O-methyl-L-rhodinose and antibacterial activity, in agreement with the assignments of the PKS domains catalyzing specific biosynthetic steps...
- Synthesis and biological evaluation of substrate-based inhibitors of 6-phosphogluconate dehydrogenase as potential drugs against African trypanosomiasis
Welsh School of Pharmacy, Redwood Building, Cardiff University, King Edward VII Avenue, CF10 3XF, Cardiff, UK
Bioorg Med Chem 11:3205-14. 2003
..The trypanocidal effect of the compounds was also evaluated in vitro against T. brucei rhodesiense as well as other related trypanosomatid parasites (i.e., Trypanosoma cruzi and Leishmania donovani)...
- Synthesis of specifically deoxygenated analogues of the methyl alpha-glycoside of the intracatenary monosaccharide repeating unit of the O-polysaccharide of Vibrio cholerae O:1
NIDDK, National Institutes of Health, Section on Carbohydrates, Bethesda, MD 20892 0815
Carbohydr Res 268:73-84. 1995
..Subsequent reaction with 2-O-benzyl-3-deoxy-L-glycero-tetronolactone, followed by hydrogenolysis of the formed tetronamido derivative, gave 24...
- Synthesis of the methyl alpha-glycosides of some isomalto-oligosaccharides specifically deoxygenated at position C-4
NIDDK, National Institutes of Health, Bethesda, MD 20892, USA
Carbohydr Res 279:133-50. 1995
- Two-step regio- and stereoselective syntheses of [19F]- and [18F]-2-deoxy-2-(R)-fluoro-beta-D-allose
Department of Nuclear Medicine, Hamilton Health Sciences, 1200 Main Street West, Hamilton, Ontario, Canada L8N 3Z5
Carbohydr Res 341:457-66. 2006
..The rapid and high radiochemical yield synthesis of 2-[(18)F]FDbetaA has potential as a probe for the bioactivity of d-allose...
- Biochemical characterization of dTDP-D-Qui4N and dTDP-D-Qui4NAc biosynthetic pathways in Shigella dysenteriae type 7 and Escherichia coli O7
TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 HongDa Street, TEDA, Tianjin 300457, People s Republic of China
J Bacteriol 189:8626-35. 2007
..This study provides valuable enzyme sources for the production of dTDP-d-Qui4N and dTDP-d-Qui4NAc, which are potentially useful in the pharmaceutical industry for drug development...
- Transferases of O-antigen biosynthesis in Salmonella enterica: dideoxyhexosyltransferases of groups B and C2 and acetyltransferase of group C2
Department of Microbiology, University of Sydney, New South Wales, Australia
J Bacteriol 177:4084-8. 1995
..enterica groups A and D and Yersinia pseudotuberculosis serovar IIA, respectively, by comparison...
- On the synthesis of the 2,6-dideoxysugar L-digitoxose
Shannon C Timmons
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3
Carbohydr Res 342:2695-704. 2007
..A novel, stereoselective synthetic route to efficiently access methyl 4-O-tert-butyldimethylsilyl-2,6-dideoxy-3-O-trimethylsilyl-alpha-l-ribo-hexopyranoside in 35% yield over nine facile steps is described...
- Synthesis of the 6-deoxytalose-containing tri- and hexasaccharides of the O-antigen polysaccharide from Mesorhizobium huakuii IFO15243T
Department of Applied Chemistry, China Agricultural University, Beijing 100 193, China
Carbohydr Res 345:2067-73. 2010
..The target oligosaccharides in the form of their p-methoxyphenyl glycosides are suitable for further glycoconjugate formation via selective cleavage of this group...
- Glycosylation inhibitors block the expression of LAV/HTLV-III (HIV) glycoproteins
H A Blough
Biochem Biophys Res Commun 141:33-8. 1986
..The reverse transcriptase was not affected by the compounds. Glycosylation inhibitors may be considered for the chemotherapy of AIDS or AIDS-related complex, or chemoprophylaxis of HIV-positive individuals...
- Atomic mapping of the sugar interactions in one-site and two-site mutants of cyanovirin-N by NMR spectroscopy
Department of Chemistry, Swedish University of Agricultural Sciences, P O Box 7015, SE 750 07 Uppsala, Sweden
Biochemistry 47:3625-35. 2008
..the 2'- and 6'-deoxy dimannosides were recognized by CV-N, whereas no binding was detected for the 3'- and 4'-deoxy sugars. These results demonstrate that the 3'- and 4'-hydroxyl groups on the terminal residue are engaged in key polar ..
- Modeling of deoxy- and dideoxyaldohexopyranosyl ring puckering with MM3(92)
W M Rockey
Department of Chemical Engineering, Iowa State University, Ames, IA 50011, USA
Carbohydr Res 335:261-73. 2001
..MM3(92) appears to overstate the prevalence of the equatorial beta anomer in all three deoxyhexoses, as earlier found with fully oxygenated aldohexopyranoses...
- Neither adrenergic nor cholinergic antagonists in the central nervous system affect 2-deoxy-D-glucose(2-DG)-induced hyperglycemia
Third Department of Internal Medicine, Nagoya University School of Medicine, Japan
Brain Res 510:321-5. 1990
..From this evidence we concluded that neither brain adrenoceptive nor cholinoceptive neurons are involved in the regulation of 2-DG-induced hyperglycemia...
- Local glucose utilization changes caused by subarachnoid contrast media in the rabbit
S E Ekholm
Department of Radiology, University of Rochester Medical Center, New York
Acta Radiol 31:209-12. 1990
..Iohexol and the control CSF solution did not cause significant effects. The results appear to indicate that iohexol has less effect on brain tissue glucose metabolism than either metrizamide or the new non-ionic dimer iodixanol...
- Elimination of contaminant Kryptofix 2.2.2 in the routine production of 2-[18F]fluoro-2-deoxy-D-glucose
S M Moerlein
Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St Louis, MO 63110
Int J Rad Appl Instrum A 40:741-3. 1989
..A thin-layer chromatographic system for the clinical screening of the radiochemical and chemical purity of this radiopharmaceutical is described...
- [Elucidation of structure of lipid A from the marine Gram-negative bacterium Pseudoalteromonas haloplanktis ATCC 14393T]
I N Krasikova
Bioorg Khim 30:409-16. 2004
- Trimethylsilylnitrate-trimethylsilyl azide: a novel reagent system for the synthesis of 2-deoxyglycosyl azides from glycals. Application in the synthesis of 2-deoxy-beta-N-glycopeptides
B Gopal Reddy
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, India
J Org Chem 69:2630-3. 2004
..reagent system comprising Me(3)SiN(3) and 20 mol % of Me(3)SiONO(2) permits conversion of glycals to 1-azido 2-deoxy sugars in one step in fair to good yields. Galactals offer higher stereoselectivities than do the glucals...
- Synthesis of N3,5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one and its 3'-deoxysugar analogue as potential anti-hepatitis C virus agents
Department of Chemistry, Pharmasset, Inc, Tucker, GA 30084, USA
Nucleosides Nucleotides Nucleic Acids 24:957-60. 2005
..It showed anti-HCV activity with EC50= 19.7 microM in replicon cells. Its 3'-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro...
- Structural studies on C-2 substitution in a new set of synthetic aminodideoxy sugars: the steric bulk at C-2 influences the puckering of the pyranose ring
Chiravakkattu G Suresh
Division of Biochemical Sciences, National Chemical Laboratory, Pune 411 008, India
Carbohydr Res 337:1507-12. 2002
..The observed variation in pyranose ring conformations in product compounds is explained in terms of C-2 substitution...
- Thymidine diphosphate-6-deoxy-L-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-L-talose from Actinobacillus actinomycetemcomitans
Department of Preventive Dentistry, Faculty of Dentistry, Kyushu University, 3 1 1 Maidashi, Higashi ku, Fukuoka 812 8582, Japan
J Biol Chem 275:6806-12. 2000
..Neither the gene for dTDP-6-deoxy-L-talose biosynthesis nor its corresponding protein product has been found in other bacteria; this biosynthetic pathway is identified here for the first time...
- Biosynthetic studies on the alpha-glucosidase inhibitor acarbose: the chemical synthesis of dTDP-4-amino-4,6-dideoxy-alpha-D-glucose
Simeon G Bowers
Department of Chemistry, University of Washington, Box 351700, Seattle, WA 98195 1700, USA
Carbohydr Res 337:297-304. 2002
..Subsequent removal of the benzyl protecting groups and reduction of the azide by hydrogenation and coupling with an activated nucleoside phosphate gave dTDP-4-amino-4,6-dideoxy-alpha-D-glucose...