Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Thiamine Disulfide. XVI. Geometrical Isomers of Thiaminic Acids
塚本 悟郎原田 清内海 勇
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ジャーナル フリー

1966 年 14 巻 8 号 p. 823-830

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Oxidation of O-benzoylthiamine disufide (I) with hydrogen peroxide in acetic acid yielded O-benzoylthiaminic acid (IIa) and its stereoisomerical compound (IIIa). It was confirmed that these two compounds were in the relation of geometrical isomers which have not yet been found in thiol-type thiamine derivatives : the compound obtained in this experiment was cis-2-(2-methy1-4-amino-5-pyrimidy) methylformamido-5-ben-zoyloxy-2-pentene-3-sulfonic acid (IIIa) of which olefin-CH3 and SO3- groups were in cis-configuration . Alkali decomposition of IIIa afforded cis-thiaminic acid (IIIb) corresponding to geometrical isomer of IIb. The configuration of these compounds was confirmed by elemental analyses, ultraviolet, infrared, nuclear magnetic resonance spectra and dissociation constants.
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© The Pharmaceutical Society of Japan
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