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

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 via (4R)-TDC.HCl intermediate. The obtained D- and L-Hcy were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides under alkaline conditions to give four stereoisomers of CYT.

authors

Shiraiwa T,Nakagawa K,Kanemoto N,Kinda T,Yamamoto H

doi

10.1248/cpb.50.1081

subject

Has Abstract

pub_date

2002-08-01 00:00:00

pages

1081-5

issue

8

eissn

0009-2363

issn

1347-5223

journal_volume

50

pub_type

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