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Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway

✍ Scribed by Emmanuel Klein; Hoàng-Oanh Nghiêm; Alain Valleix; Charles Mioskowski; Luc Lebeau

Book ID
101369339
Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
149 KB
Volume
8
Category
Article
ISSN
0947-6539

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✦ Synopsis

Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebis-phosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.

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