| Synthesis and NMR spectroscopy of nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids. | |
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MedLine Citation:
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PMID: 11595217 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids are essential constituents of some bacterial polysaccharides and glycoproteins. In order to establish reliably the configuration of the natural sugars, nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids were synthesized, including di-N-acetyl-legionaminic and -pseudaminic acids (the D-glycero-D-galacto and L-glycero-L-manno isomers, respectively) and their isomers at C-4, C-5, C-7, and C-8 having the L-glycero-D-galacto, D-glycero-D-talo, L-glycero-D-talo, D-glycero-L-altro, L-glycero-L-altro, D-glycero-L-manno, and L-glycero-L-gluco configurations. Synthesis was performed by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-gulose, -D-mannose, -D-talose, and -L-allose with oxalacetic acid under basic conditions, the reaction of the last two precursors being accompanied by epimerisation at C-2. The 1H and 13C NMR data of the synthetic compounds are discussed. Acetylated methyl esters of the C-7 and C-8 isomeric nonulosonic acids were prepared and used for analysis of the side-chain conformation by NMR spectroscopy. |
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Authors:
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Y E Tsvetkov; A S Shashkov; Y A Knirel; U Zähringer |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Carbohydrate research Volume: 335 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 2001 Oct |
Date Detail:
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Created Date: 2001-10-11 Completed Date: 2002-01-29 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: Netherlands |
Other Details:
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Languages: eng Pagination: 221-43 Citation Subset: IM |
Affiliation:
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N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, 119991 Moscow, Russian Federation. tsvetkov@ioc.ac.ru |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Gluconates
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chemical synthesis*,
chemistry Glucose / chemistry Magnetic Resonance Spectroscopy Mannose / chemistry Oxaloacetic Acids / chemistry Polysaccharides, Bacterial / chemistry* Sialic Acids / chemical synthesis, chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Gluconates; 0/Oxaloacetic Acids; 0/Polysaccharides, Bacterial; 0/Sialic Acids; 112154-63-9/5,7-diacetamido-3,5,7,9-tetradeoxy-glycerogalacto-nonulosonic acid; 31103-86-3/Mannose; 50-99-7/Glucose; 6038-51-3/allose |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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