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Synthesis ofS-(Carboxymethyl)-d-cysteine by 3-chloro-d-alanine chloride-lyase ofPseudomonas putida CR 1-1
Authors:Toru Nagasawa  Hidekazu Hosono  Haruyuki Ohkishi  Hideaki Yamada
Affiliation:1. Department of Agricultural Chemistry, Kyoto University, 606, Kyoto, Japan
2. Research Center for Cell and Tissue Culture, Kyoto University, 606, Kyoto, Japan
Abstract:S-(Carboxymethyl)-d-cysteine, which is an important component of semisynthetic cephalosporin, MT-141, was enzymatically synthesized.S-(Ethoxy-carbonyl-methyl)-d-cystein was synthesized from 3-chloro-d-alanine and ethyl thioglycolate by the β-replacement reaction of 3-chloro-d-alanine chloride-lyase fromPseudomonas putida CR 1-1 and subsequently hydrolyzed by alkali. The synthesizedS-(carboxymethyl)-d-cysteine was isolated from a large scale reaction mixture and identified physicochemically. The reaction conditions for the synthesis ofS-(ethoxycarbonylmethyl)-d-cysteine were optimized using resting cells ofP. putida CR 1-1.
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