| Structural modification induced in heparin by a Fenton-type depolymerization process. | |
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MedLine Citation:
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PMID: 17629843 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A low molecular weight heparin (LMWH) obtained by a depolymerization process induced by a Fenton-type reagent was characterized in depth by nuclear magnetic resonance (NMR) spectroscopy. The depolymerization involves the cleavage of glycosidic bonds, leading to natural terminal reducing end residues, mainly represented by N-sulfated glucosamine (A (NS)). Natural uronic acids, especially the 2- O-sulfate iduronic acid (I (2S)), are also present as reducing residues. A peculiar reaction results, such as the disappearance of the nonsulfated iduronic acid residues when followed by 6-O-nonsulfated glucosamine, and the decrease of the glucuronic acid when followed by the N-acetylglucosamine, were observed. Iduronic acid residues, followed by 6- O-sulfate glucosamine (A (Nx,6S)), and the glucuronic acid residues, followed by A (NS) residues, were not modified. A few minor internal chain modifications occur, possibly arising from oxidative breaking of the bond between C2-C3 of glucosamine and uronic acids, suggested by evidence of formation of new -COR groups. Finally, no change was observed in the content of the N-sulfated, 6-O-sulfated glucosamine bearing an extra sulfate on 3-O, which is considered the marker of the active site for antithrombin. With respect to the original heparin, this LMWH is characterized by a lower number of nonsulfated uronic acid residues, and as a consequence, by a lower degree of structural heterogeneity than LMWHs prepared with other procedures. |
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Authors:
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Elena Vismara; Monica Pierini; Sara Guglieri; Lino Liverani; Giuseppe Mascellani; Giangiacomo Torri |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Review |
Journal Detail:
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Title: Seminars in thrombosis and hemostasis Volume: 33 ISSN: 0094-6176 ISO Abbreviation: Semin. Thromb. Hemost. Publication Date: 2007 Jul |
Date Detail:
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Created Date: 2007-07-16 Completed Date: 2007-09-27 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0431155 Medline TA: Semin Thromb Hemost Country: United States |
Other Details:
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Languages: eng Pagination: 466-77 Citation Subset: IM |
Affiliation:
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G. Natta Chemistry Department, Polytechnic of Milan, V. Mancinelli 7, 20131 Milan, Italy. elena.vismara@polimi.it |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Free Radicals
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chemistry* Heparin, Low-Molecular-Weight / chemistry* Iduronic Acid / chemistry* Molecular Structure Oxidation-Reduction |
| Chemical | |
Reg. No./Substance:
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0/Free Radicals; 0/Heparin, Low-Molecular-Weight; 3402-98-0/Iduronic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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