ビタミンB_6誘導体の研究 : (X)ピリドキサールおよびピリドキサールリン酸とホモシステインエステルの結合化合物の合成とその理化学的性質

概要

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Several derivatives of 2-(3-hydroxy-5-hydroxymethyl-2-methylpyridyl-4)-tetrahydro-1,3-thiazine-4-carboxylic acid (PAL-HCySH) and 2-(3-hydroxy-2-methyl-5-phosphoryloxymethyl-pyridyl-4)-tetrahydro-1,3-thiazine-4-carboxylic acid (PAL-P-HCySH), which have potential vitamin B_6 activity, were synthesized. Alkylesters of PAL-HCySH, and PAL-P-HCySH were prepared in 12-70% yield by the reactions of pyridoxal or pyridoxal phosphate with alkyl DL-homocysteinates which were obtained from the ring-cleavage of DL-homocysteine thiolactone-HCl with sodium alcoxides in the corresponding alcohols. The acetylations of methyl 2-(3-hydroxy-5-hydroxymethyl-2-methylpyridyl-4)-tetrahydro-1,3-thiazine-4-carboxylate (PAL-HCySOMe) with acetic anhydride were also investigated. The alcoholic O-acylates (acetate, benzoate, butyrate, and nicotinate) of PAL-HCySH were prepared by the condensation of pyridoxal-5-acylates with DL-homocysteine in high yield. Further, the spectrophotometric studies of the stabilities and dissociations of PAL-HCySOMe, 2-(5-acetoxymethyl-3-hydroxy-2-methylpyridyl-4)-tetrahydro-1,3-thiazine-4-carboxylic acid (PAL-5-Ac-HCySH) and methyl 2-(5-acetoxymethyl-3-hydroxy-2-methylpyridyl-4)-tetrahydro-1,3-thiazine-4-carboxylate (PAL-5-Ac-HCySOMe) were carried out to compare with those of PAL-HCySH.
日本ビタミン学会の論文
1968-06-25