Synthesis of S-(carboxymethyl)-D-cysteine by 3-chloro-D-alanine chloride-lyase of pseudomonas putida CR 1-1.
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 beta-replacement reaction of 3-chloro-D-alanine chloride-lyase from Pseudomonas putida CR 1-1 and subsequently hydrolyzed by alkali. The synthesized S-(carboxymethyl)-D-cysteine was isolated from a large scale reaction mixture and identified physicochemically. The reaction conditions for the synthesis of S-(ethoxycarbonylmethyl)-D-cysteine were optimized using resting cells of P. putida CR 1-1.
D002233:Carbocysteine / Q000096:biosynthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003545:Cysteine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D007700:Kinetics; D008190:Lyases / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D011549:Pseudomonas / Q000201:enzymology*; D013055:Spectrophotometry, Infrared
D007202:Indicators and Reagents; D002233:Carbocysteine; D008190:Lyases; C031729:3-chloro-D-alanine dehydrochlorinase; D003545:Cysteine