Open AccessPreparation of Chiral 2-chloromandelamide: Stereoselective Reduction of an Aromatic α-keto Amide with Actinomycete Strains
Author(s) -
Kohji Ishihara,
Mai Nishimura,
Ken Ichi Nakashima,
Noriko Machii,
F Miyake,
Miyuki Nishi,
Momoko Yoshida,
Noriyoshi Masuoka,
Nobuyoshi Nakajima
Publication year - 2010
Publication title -
biochemistry insights.
Language(s) - English
Resource type - Journals
ISSN - 1178-6264
DOI - 10.4137/bci.s4231
Subject(s) - amide , thermophile , stereoselectivity , mesophile , chemistry , streptomyces , enantiomer , enantiomeric excess , biotransformation , glycerol , stereochemistry , organic chemistry , bacteria , biology , catalysis , enantioselective synthesis , enzyme , genetics
The stereoselective reduction of an aromatic α-keto amide with actinomycete strains was investigated. It was found that 2-chlorobenzoylformamide was reduced to the corresponding 2-chloromandelamide by mesophilic and thermophilic strains of actinomycetes. Among the strains tested, the reduction of 2-chlorobenzoylformamide by Streptomyces thermocyaneoviolaceus (one of thermophilic strains) in the presence of glycerol as an additive produced only ( S )-2-chloromandelamide in >99% conversion with >99% enantiomeric excess (e.e.). On the other hand, the reduction by Streptomyces thermocarboxydovorans NBRC16324 at 45 °C or Thermoactinomyces vulgaris NBRC15851 cultivated in a soluble starch-based medium gave the corresponding ( R )-hydroxy amide (conversion, 99%; >99% e.e.). Mesophilic and other thermophilic actinomycete strains also catalyzed the reduction to the corresponding (R)-hydroxy amide with 85%–>99% e.e. Thus, the syntheses of both enantiomers of 2-chloromandelamide was achieved though the reduction of 2-chlorobenzoylformamide with different actinomycete strains