| 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. | |
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MedLine Citation:
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PMID: 9742689 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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S Yamada; M Watanabe; K Sugahara |
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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: 309 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 1998 Jul |
Date Detail:
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Created Date: 1998-10-29 Completed Date: 1998-10-29 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: 261-8 Citation Subset: IM |
Affiliation:
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Department of Biochemistry, Kobe Pharmaceutical University, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Disaccharides / chemistry*, isolation & purification Heparin / chemistry* Heparin Lyase Hexosamines / chemistry* Magnetic Resonance Spectroscopy / methods Oligosaccharides / chemistry* Protons Stereoisomerism Sulfuric Acid Esters / chemistry* |
| Chemical | |
Reg. No./Substance:
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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 4.2.2.7/Heparin Lyase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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