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논문 기본 정보
- 자료유형
- 학술저널
- 저자정보
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- 한국미생물생명공학회 Journal of Microbiology and Biotechnology Journal of Microbiology and Biotechnology 제23권 제10호
- 발행연도
- 2013.1
- 수록면
- 1,395 - 1,402 (8page)
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Reductases convert some achiral ketone compounds into chiral alcohols, which are important materials for the synthesis of chiral drugs. The Saccharomyces cerevisiae reductase YOR120W converts ethyl-4-chloro-3-oxobutanoate (ECOB) enantioselectively into (R)-ethyl-4-chloro-3-hydroxybutanoate ((R)-ECHB), an intermediate of a pharmaceutical. As YOR120W requires NADPH as a cofactor for the reduction reaction, a cofactor recycling system using Bacillus subtilis glucose dehydrogenase was employed. Using this coupling reaction system, 100 mM ECOB was converted to (R)-ECHB. A homology modeling and site-directed mutagenesis experiment were performed to determine the NADPH-binding site of YOR120W. Four residues (Q29, K264, N267, and R270) were suggested by homology and docking modeling to interact directly with 2’-phosphate of NADPH. Among them, two positively charged residues (K264 and R270) were experimentally demonstrated to be necessary for NADPH 2’-phosphate binding. A mutant enzyme (Q29E) showed an enhanced enantiomeric excess value compared with that of the wild-type enzyme.
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참고문헌 (20)
참고문헌 신청
Aragozzini F / 1992 / Biocatalytic, enantioselective preparations of (R)- and (S)-ethyl 4-chloro-3-hydroxybutanoate, a useful chiral synthon / Biocatal. Biotransform 5 : 325
Campbell E / 2010 / Broadening the cofactor specificity of a thermostable alcohol dehydrogenase using rational protein design introduces novel kinetic transient behavior / Bi
Choi YH / 2010 / Asymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity / Appl. Microbiol. Biotechnol
Cundari TR / 2007 / . A molecular modeling study on the enantioselectivity of aryl alkyl ketone reductions by a NADPH-dependent carbonyl reductase / J. Mol. Model 13 : 685 ~
Goldberg K / 2007 / Biocatalytic ketone reduction - a powerful tool for the production of chiral alcohols. Part I: processes with isolated enzymes / Appl. Microbiol. Biotechn
Campbell E / 2010 / Broadening the cofactor specificity of a thermostable alcohol dehydrogenase using rational protein design introduces novel kinetic transient behavior / Bi
Choi YH / 2010 / Asymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity / Appl. Microbiol. Biotechnol
Cundari TR / 2007 / . A molecular modeling study on the enantioselectivity of aryl alkyl ketone reductions by a NADPH-dependent carbonyl reductase / J. Mol. Model 13 : 685 ~
Goldberg K / 2007 / Biocatalytic ketone reduction - a powerful tool for the production of chiral alcohols. Part I: processes with isolated enzymes / Appl. Microbiol. Biotechn
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