- 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...
- 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...
- 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...
- 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)...
- 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...
- 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...
- 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)...
- 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
- 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...
- 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...
- Structural analysis of the exopolysaccharide from Burkholderia caribensis strain MWAP71
, , B.P.53, F-38041, Grenoble, France
Carbohydr Res 334:127-33. 2001
- 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...
- [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...
- 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
- 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...
- 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
- 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...
- 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...
- 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...
- 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...
- 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
- 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
- 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...
- 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...
- 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...
- 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...
- 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
- 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 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...
- 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...
- 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...
- [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...
- 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
- 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]..
- 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
- 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...
- 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...
- 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...
- 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)...
- 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...
- 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
- 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 ..
- 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...
- 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
- 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...
- 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 ..
- 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...
- 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 ..
- 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...
- 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...
- [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
- 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
- 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 ..
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- Robotic production of 2-deoxy-2-[18F]fluoro-D-glucose: a routine method of synthesis using tetrabutylammonium [18F]fluoride
J W Brodack
Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St Louis, MO 63110
Int J Rad Appl Instrum A 39:699-703. 1988
..The procedure is a modification of the synthesis reported by Hamacher et al. [Hamacher et al. (1986) J. Nucl. Med. 27, 235]...
- Sequence analysis of the sulfated rhamno-oligosaccharides derived from a sulfated rhamnan
Key Laboratory of Marine Drugs, Ministry of Education, Institute of Marine Drug and Food, Ocean University of China, Qingdao 266003, People s Republic of China
Carbohydr Polym 90:1299-304. 2012
- PCP-induced alterations in cerebral glucose utilization in rat brain: blockade by metaphit, a PCP-receptor-acylating agent
C A Tamminga
Experimental Therapeutics Branch, NINCDS, Bethesda, MD 20892
Synapse 1:497-504. 1987
..These results indicate an antagonist effect of metaphit on the PCP system and suggest a widespread action of metaphit, putatively at a PCP-related site, possibly in connection with the N-methyl-D-aspartate (NMDA) receptor...
- Specific alterations in cardiovascular function and in glucose utilisation within lower brainstem nuclei following intracisternal neuropeptide Y in the conscious rat
I M Macrae
University Department of Materia Medica, Stobhill General Hospital, Glasgow, UK
Brain Res 515:99-103. 1990
..It is proposed that the area postrema, nucleus tractus solitarius and Kolliker-Fuse nucleus in the brainstem are involved functionally in the haemodynamic response to i.c. NPY...
- Structural analysis and biosynthesis gene cluster of an antigenic glycopeptidolipid from Mycobacterium intracellulare
Department of Host Defense, Osaka City University Graduate School of Medicine, 1 4 3 Asahi machi, Abeno Ku, Osaka 545 8585, Japan
J Bacteriol 190:3613-21. 2008
..253 containing gtfB-drrC of M. intracellulare serotype 16, and the transformant produced serotype 16 GPL. Together, the ORFs of this serotype 16-specific gene cluster are responsible for the biosynthesis of serotype 16 GPL...
- 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...
- 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...
- Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization
William W Cutchins
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322
Org Lett 4:749-52. 2002
..reaction: see text] A stereoselective synthesis of the C-3 branched amino glycals of vancosamine and saccharosamine is described that features a tungsten carbonyl catalyzed cycloisomerization of the corresponding alkynyl alcohol...
- 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...
- 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...
- Galacto, gluco, manno, and disaccharide-based C-glycosides of 2-amino-2-deoxy sugars
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK
Org Lett 4:4623-5. 2002
..This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.
- Characterization of the GDP-D-mannose biosynthesis pathway in Coxiella burnetii: the initial steps for GDP-β-D-virenose biosynthesis
Craig T Narasaki
Texas A and M University Health Science Center, College of Medicine, College Station, Texas, United States of America
PLoS ONE 6:e25514. 2011
..A fundamental understanding of C. burnetii genes that encode PMI, PMM and GMP is critical to fully understand the biosynthesic pathway of GDP-β-D-virenose and LPS structure in C. burnetii...
- Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA
J Org Chem 76:9193-209. 2011
- Characterization of the lipopolysaccharide from Pasteurella multocida Heddleston serovar 9: identification of a proposed bi-functional dTDP-3-acetamido-3,6-dideoxy-α-D-glucose biosynthesis enzyme
Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Department of Microbiology, Monash University, Melbourne 3800, Australia
Glycobiology 22:332-44. 2012
- C-Glycosides of 2-amino-2-deoxy sugars. beta-C-Glycosides and 1,1-disubstituted variants
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK
Org Lett 6:2445-8. 2004
- A practical method for the stereoselective generation of beta-2-deoxy glycosyl phosphates
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA
Org Lett 6:2873-6. 2004
..Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products.
- Investigating Mithramycin deoxysugar biosynthesis: enzymatic total synthesis of TDP-D-olivose
Department of Pharmaceutical Sciences, University of Kentucky, Lexington, KY 40536 0596, USA
Chembiochem 12:2568-71. 2011
..The results also revealed that MtmC is a bifunctional enzyme that can perform a 4-ketoreduction necessary for D-olivose biosynthesis besides the previously found C-methyltransfer for D-mycarose biosynthesis...
- Structural characterization of trimethylsilyl methyl glycosides derivatives by high-resolution mass spectrometry, linked scans and MIKE experiments
COBRA IRCOF, UFR des Sciences, Universite de Rouen, CNRS UMR 6014, 76821, Mont Saint Aignan Cedex, France
Anal Bioanal Chem 390:1853-60. 2008
..investigations have been carried out for the structural analysis of trimethylsilyl methyl derivatives of keto-deoxy sugars and sialic acids studied under electron ionization. Fragmentation patterns were determined...
- Attachment of Agrobacterium tumefaciens to carrot cells and Arabidopsis wound sites is correlated with the presence of a cell-associated, acidic polysaccharide
B L Reuhs
Complex Carbohydrate Research Center, University of Georgia, Athens 30602 4712, USA
J Bacteriol 179:5372-9. 1997
..This indicates that the acidic polysaccharide may play a role in the attachment of A. tumefaciens to host soma plant cells...
- Locus coeruleus input affects glucose metabolism in activated rat barrel cortex
R L Craik
Department of Physical Therapy, Beaver College, Glenside, PA 19038
Brain Res Bull 19:495-9. 1987
..This suggests a predominantly inhibitory role for NE in modulating SmI oxidative metabolism during physiologic stimulation...
- An attempt to localize the lumbar locomotor generator in the rabbit using 2-deoxy-[14C]glucose autoradiography
Laboratoire de Neurophysiologie, UA C N R S 1199, Faculte des Sciences Mirande, Dijon, France
Neurosci Lett 86:139-43. 1988
..Compared to spinal control preparations not activated pharmacologically, the treated animals showed a specific labeling in the intermediate part of the grey matter, extending from L6 to S1...
- Organization of the biosynthetic gene cluster for the macrolide antibiotic spiramycin in Streptomyces ambofaciens
CNRS UMR8621, Universite Paris Sud, Institut de Genetique et Microbiologie, Batiment 400, F 91405 Orsay cedex, France
Microbiology 153:4111-22. 2007
..This work reveals the main features of spiramycin biosynthesis and constitutes a first step towards a detailed molecular analysis of the production of this medically important antibiotic...
- Effect of peptide YY on insulin release stimulated by 2-deoxyglucose and neuropeptides in dogs
Y S Guo
Department of Surgery, University of Texas Medical Branch, Galveston 77550
Pancreas 3:128-34. 1988
..These results demonstrated that PYY might inhibit the cephalic phase of insulin release from dogs triggered by 2-DG and by the neuropeptides GRP and G4. Thus, PYY may play a negative feedback regulatory role on insulin release...
- Tegumental glucose permeability in male and female Schistosoma mansoni
E M Cornford
Comprehensive Epilepsy Program, V A Wadsworth Medical Center, Los Angeles, California 90073
J Parasitol 74:116-28. 1988
..Gender- and mating-specific analyses of PS products indicate that tegumental permeability to glucose is significantly increased in mated schistosomes, and compares very favorably to that of the host liver...
- Intestinal absorption of two glucose analogues in rats of different ages
W C Eastin
Toxicology Research and Testing Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Exp Gerontol 22:351-7. 1987
..There appears to be a gradual decrease in net active transport of glucose with age. The mechanism responsible for this age-related change remains to be explained...
- Substrate specificity of small-intestinal lactase: study of the steric effects and hydrogen bonds involved in enzyme-substrate interaction
Instituto de Quimica Organica, Consejo Superior de Investigaciones Cientificas, Madrid, Spain
Carbohydr Res 271:31-42. 1995
..Now we have found that the corresponding fluorine derivatives are not, or very poorly, recognized. This suggests that the HO-3' and HO-6 participate, as donors, in hydrogen bonds in the interaction with the enzyme...
- 3H-2-deoxyglucose uptake after electrical stimulation of cardioactive sites in insular cortex and mediodorsal nucleus of the thalamus in rabbits
S L Buchanan
Neuroscience Laboratory, Wm Jennings Bryan Dorn Veterans Hospital, Columbia, SC 29201
Brain Res Bull 19:439-52. 1987
..A more significant finding however, was that the reciprocal connections of MD and Ins appear to be activated by stimulation of either structure, even though their relationship to autonomic function appears to be quite different...
- The chemical structure and genetic locus of Campylobacter jejuni CG8486 (serotype HS:4) capsular polysaccharide: the identification of 6-deoxy-D-ido-heptopyranose
Yu Han Chen
Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1
Carbohydr Res 343:1034-40. 2008
..jejuni HS:4 CPS complex. The efficacy of a glycoconjugate vaccine based on C. jejuni CG8486 CPS is presently being tested in an animal model, the results of which will be presented in future communications...
- Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Carbohydr Res 346:1569-75. 2011
..However, when thiol was used as an acceptor, only a stereoselective addition at C-3 resulted, so as to form C-1, C-3 dithio-substituted 2-deoxypyranosides...
- Distribution of dTDP-glucose-4,6-dehydratase gene and diversity of potential glycosylated natural products in marine sediment-derived bacteria
Key Laboratory of Biotechnology of Antibiotics, Ministry of Health, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences CAMS and Peking Union Medical College PUMC, Beijing, China
Appl Microbiol Biotechnol 90:1347-59. 2011
..The rapid identification of strains that possess dTGD gene provides a bioinformatics assessment of the greatest potential to produce glycosylated compounds despite the absence of fully biosynthetic pathways or genome sequences...
- The genetics and structure of the O-specific polysaccharide of Yersinia pseudotuberculosis serotype O:10 and its relationship with Escherichia coli O111 and Salmonella enterica O35
Johanna J Kenyon
Division of Microbiology, School of Molecular Bioscience, University of Sydney, Sydney 2006, Australia
Glycobiology 21:1131-9. 2011
..pseudotuberculosis O:10, although there is significant conservation of gene order. Within Y. pseudotuberculosis, the O10 structure is most closely related to the O:6 and O:7 structures...
- Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties
Micah D Shepherd
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY 40536 0596, USA
Appl Environ Microbiol 77:435-41. 2011
..Our findings demonstrate GilGT to be a moderately flexible C-glycosyltransferase able to transfer both D- and L-hexopyranose moieties to the unique angucyclinone-derived benzo[D]naphtho[1,2b]pyran-6-one backbone of the gilvocarcins...
- Glycosyl hydroperoxides derived from 2-deoxysugars
Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44 52, 01 224 Warsaw, Poland
Carbohydr Res 345:2464-8. 2010
..Separation of the α - and β-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection...