Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine.

T Shiraiwa, K Nakagawa, N Kanemoto…

Index: Shiraiwa, Tadashi; Nakagawa, Kazuo; Kanemoto, Norito; Kinda, Tomohiro; Yamamoto, Hiroki Chemical and Pharmaceutical Bulletin, 2002 , vol. 50, # 8 p. 1081 - 1085

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Citation Number: 10

Abstract

In order to synthesize four stereoisomers of cystathionine (CYT), D-and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)- 1, 3-thiazane-2, 4-dicarboxylic acid hydrochloride [(4S)-TDC· HCl]. L-Hcy was obtained by treatment of (4S)-TDC· HCl with hydroxylamine. D-Hcy was also synthesized from D-Met ...