Studies on pyrimidine derivatives and related compounds. Liv. st]Reaction of thiamine with phenylglyoxal and synthesis of hydroxymethylthiamine

✍ Scribed by Akira Takamizawa; Saichi Matsumoto; Shoji Sakai

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 244 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89717-8

✦ Synopsis

In relation to the mechanism of thiamine action, the chemical reactivity of C-2 carbon atom of the thiazolium portion of thiamine molecule has recently attmcted considerable attentions (1). Previously, the authors reported on the reaction of thiamine with aldehydes involving anomolous C-acylation at the 2-position of the thiazolium nucleus (2). This communication describes a new reaction of thiamine with phenylglyoxal and a synthesis of hydroxymethylthiamine, a postulated intermediate in the glyoxylate metabolism (3). Ethanolic suspension of thiamine-sodium salt (I) readily reacted with phenylglyoxal in the presence of carbon dioxide at room temperature to give a yellow crystalline compound II, m.p. 150-158O (d.), as hemihydrate C,H,N@$.'/,HzO,** in 50-60% yield accompanied with thiamine-thiazolone (III)