147331-82-6Relevant articles and documents
Preparations of Optically Active Homocysteine and Homocystine by Asymmetric Transformation of (RS)-1,3-Thiazane-4-carboxylic Acid
Miyazaki, Hideya,Ohta, Atsushi,Kawakatsu, Nobuyuki,Waki, Yukitaka,Gogun, Yasuhiro,et al.
, p. 536 - 540 (2007/10/02)
DL-Homocysteine from (RS)-homocysteine thiolactone hydrochloride was subjected to reaction with formaldehyde in acetic acid to give (RS)-1,3-thiazane-4-carboxylic acid monohydrate .An asymmetric transformation of (RS)-THA*H2O was achieved via salt formation with optically active tartaric acid in the presence of salicylaldehyde in acetic acid.The (R)- and (S)-THA obtained, respectively, from the salt of (R)-THA with (2R,3R)-tartaric acid and its enantiomeric salt were treated with hydroxylamine hydrochloride to give D- and L-Hcy of 100percent optical purity, respectively, in 50percent yield from (RS)-HTL*HCl.Oxidation of D- and L-Hcy with hydrogen peroxide gave D- and L-homocystine, respectively, in 47percent yield.
