Photochemical preparation of a novel low molecular weight heparin

Higashi, Kyohei
Hosoyama, Saori
Ohno, Asami
Masuko, Sayaka
Yang, Bo
Sterner, Eric
Wang, Zhenyu
Linhardt, Robert J.
Toida, Toshihiko
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Photochemical preparation of a novel low molecular weight heparin, K. Higashi, S. Hosoyama, A. Ohno, S. Masuko, B. Yang, E. Sterner, Z. Wang, R. J. Linhardt, T. Toida, Carbohydrate Polymers, 87, 1737-1743, 2012.
Commercial low molecular weight heparins (LMWHs) are prepared by several methods including peroxidative cleavage, nitrous acid cleavage, chemical ß-elimination, and enzymatic β-elimination. The disadvantages of these methods are that strong reaction conditions or harsh chemicals are used and these can result in decomposition or modification of saccharide units within the polysaccharide backbone. These side-reactions reduce product quality and yield. Here we show the partial photolysis of unfractionated heparin can be performed in distillated water using titanium dioxide (TiO2). TiO2 is a catalyst that can be easily removed by centrifugation or filtration after the photochemical reaction takes place, resulting in highly pure products. The anticoagulant activity of photodegraded LMWH (pLMWH) is comparable to the most common commercially available LMWHs (i.e., Enoxaparin and Dalteparin). 1H NMR spectra obtained show that pLMWH maintains the same core structure as unfractionated heparin. This photochemical reaction was investigated using liquid chromatography/mass spectrometry (LC/MS) and unlike other processes commonly used to prepare LMWHs, photochemically preparation affords polysaccharide chains of reduced length having both odd and even of saccharide residues.
Carbohydrate Polymers, 87, 1737-1743
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Carbohydrate Polymers
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