Document Detail

Structural modification induced in heparin by a Fenton-type depolymerization process.
MedLine Citation:
PMID:  17629843     Owner:  NLM     Status:  MEDLINE    
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.
Elena Vismara; Monica Pierini; Sara Guglieri; Lino Liverani; Giuseppe Mascellani; Giangiacomo Torri
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review    
Journal Detail:
Title:  Seminars in thrombosis and hemostasis     Volume:  33     ISSN:  0094-6176     ISO Abbreviation:  Semin. Thromb. Hemost.     Publication Date:  2007 Jul 
Date Detail:
Created Date:  2007-07-16     Completed Date:  2007-09-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0431155     Medline TA:  Semin Thromb Hemost     Country:  United States    
Other Details:
Languages:  eng     Pagination:  466-77     Citation Subset:  IM    
G. Natta Chemistry Department, Polytechnic of Milan, V. Mancinelli 7, 20131 Milan, Italy.
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MeSH Terms
Free Radicals / chemistry*
Heparin, Low-Molecular-Weight / chemistry*
Iduronic Acid / chemistry*
Molecular Structure
Reg. No./Substance:
0/Free Radicals; 0/Heparin, Low-Molecular-Weight; 3402-98-0/Iduronic Acid

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