Document Detail

Conversion of N-sulfated glucosamine to N-sulfated mannosamine in an unsaturated heparin disaccharide by non-enzymatic, base-catalyzed C-2 epimerization during enzymatic oligosaccharide preparation.
MedLine Citation:
PMID:  9742689     Owner:  NLM     Status:  MEDLINE    
A novel disaccharide was isolated beside the predominant trisulfated disaccharide, delta HexA(2-O-sulfate)(alpha 1-4)GlcN(2-N-,6-O-disulfate) (delta HexA and GlcN represent 4-deoxy-alpha-L-threo-hex-4-enepyranosyluronic acid and D-glucosamine, respectively) after treatment of porcine intestinal heparin with Flavobacterium heparinase. It accounted for 18% of total disaccharides. The structure was characterized by secondary ion mass spectrometry, enzymatic digestions, amino sugar analysis, and 500 MHz one- and two-dimensional 1H NMR spectroscopy as delta HexA(2-O-sulfate) (alpha 1-4)ManN(2-N-,6-O-disulfate), where ManN represents D-mannosamine. The C-2 epimerization from delta HexA(2-O-sulfate) (alpha 1-4)GlcN(2-N-,6-O-disulfate) to delta HexA(2-O-sulfate) (alpha 1-4)ManN(2-N-,6-O-disulfate) was also demonstrated to take place in vitro under very mild alkaline conditions. Hence, the latter compound is not a biosynthetic product, but is most likely an artifact generated by non-enzymatic, base-catalyzed C-2 epimerization during enzymatic preparation of heparin oligosaccharides. The present results warn that the formation of the C-2 epimerized compound has to be circumvented in the structural analysis of heparin/heparan sulfate.
S Yamada; M Watanabe; K Sugahara
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  309     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1998 Jul 
Date Detail:
Created Date:  1998-10-29     Completed Date:  1998-10-29     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  261-8     Citation Subset:  IM    
Department of Biochemistry, Kobe Pharmaceutical University, Japan.
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MeSH Terms
Disaccharides / chemistry*,  isolation & purification
Heparin / chemistry*
Heparin Lyase
Hexosamines / chemistry*
Magnetic Resonance Spectroscopy / methods
Oligosaccharides / chemistry*
Sulfuric Acid Esters / chemistry*
Reg. No./Substance:
0/4-deoxy-2-sulfooxy-threo-hex-4-enepyranosyluronic acid-1-4-(N,6-disulfooxyglucosamine); 0/Disaccharides; 0/Hexosamines; 0/Oligosaccharides; 0/Protons; 0/Sulfuric Acid Esters; 2636-92-2/mannosamine; 9005-49-6/Heparin; EC Lyase

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