YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Vitamin B1及び諸関係化合物の研究 (第45報)
シオール型Vitamin B1誘導体について その1
松川 泰三川崎 弌
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1953 年 73 巻 7 号 p. 705-708

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Application of acylation agent, such as benzoyl chloride, acetic anhydride, and p-nitrobenzoyl chloride, to the thiol-type vitamin B1 respectively yielded crystals of m. p. 173-174° (decomp.) (VII), m. p. 122-123° (decomp.) (VIII), and m. p. 135° (decomp.) (IX). These compounds gave negative thiochrome reaction but the reaction became positive after treatment with acid or alkali. From such facts and from their elemental analytical values, they were respectively assumed as 2-methyl-4-amino-5-[N-(3′-benzoylmer-capto-5′- benzoy-Δ2′-pentenyl-2′)]-formaminomethylpyrimidine (VII), (O, S-dibenzoyl B1) 2-methyl-4-amino-5-[N-(3′-acetylmercapto-5′-acetoxy-Δ2′-pentenyl-2′)]-formaminomethyl-pyrimidine (VIII) (O, S-diacetyl B1), and 2-methyl-4-amino-5-[N-(3′-p-nitrobenzoylmercapto-5′-hydroxy-Δ2′-pentenyl-2′)]-formaminomethylpyrimidine (IX) (S-p-nitrobenzoyl B1). These compounds were tested for the prevention of B1-deficiency in Uroloncha domestica and were found to have almost equal efficacy as vitamin B1. It was also found that the absorption of (VII) and (VIII) through the alimentary canal was better compared to vitamin B1. Since (VIII) is easily formed from vitamin B1 and vice versa, it may be assumed that, as a part of biochemical actions of vitamin B1, the pyrophosphate of S-acetyl B1 undergoes transacetylation and acetylates coenzyme A to form acetylcoenzyme A.

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