Document Detail

Synthesis and NMR spectroscopy of nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids.
MedLine Citation:
PMID:  11595217     Owner:  NLM     Status:  MEDLINE    
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.
Y E Tsvetkov; A S Shashkov; Y A Knirel; U Zähringer
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  335     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2001 Oct 
Date Detail:
Created Date:  2001-10-11     Completed Date:  2002-01-29     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  221-43     Citation Subset:  IM    
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, 119991 Moscow, Russian Federation.
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MeSH Terms
Gluconates / chemical synthesis*,  chemistry
Glucose / chemistry
Magnetic Resonance Spectroscopy
Mannose / chemistry
Oxaloacetic Acids / chemistry
Polysaccharides, Bacterial / chemistry*
Sialic Acids / chemical synthesis,  chemistry
Reg. No./Substance:
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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