Highly enantioselective and efficient synthesis of methyl (R)-o-chloromandelate with recombinant E. coli: toward practical and green access to clopidogrel.
Methyl (R)-o-chloromandelate ((R)-), which is an intermediate for a platelet aggregation inhibitor named clopidogrel, was obtained in >99% ee by the asymmetric reduction of methyl o-chlorobenzoylformate (2) (up to 1.0 M) with recombinant E. coli overproducing a versatile carbonyl reductase.
Ema
Tadashi
T
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan. ema@cc.okayama-u.ac.jp
Okita
Nobuyasu
N
Ide
Sayaka
S
Sakai
Takashi
T
D000429:Alcohol Oxidoreductases / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D001711:Biotransformation; D000077144:Clopidogrel; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics / Q000378:metabolism*; D007218:Industrial Microbiology; D008333:Mandelic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013988:Ticlopidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D008333:Mandelic Acids; D010648:Phenylacetates; C522563:methyl 2-chlorobenozylformate; C522562:methyl 2-chloromandelate; D000077144:Clopidogrel; D000429:Alcohol Oxidoreductases; D013988:Ticlopidine