- Electronic Effect-Guided Rational Design of Candida antarctica Lipase B for Kinetic Resolution Towards Diarylmethanols
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Herein, we developed an electronic effect-guided rational design strategy to enhance the enantioselectivity of Candida antarctica lipase B (CALB) mutants towards bulky pyridyl(phenyl)methanols. Compared to W104A mutant previously reported with reversed S-stereoselectivity toward sec-alcohols, three mutants (W104C, W104S and W104T) displayed significant improvement of S-enantioselectivity in the kinetic resolution (KR) of various phenyl pyridyl methyl acetates due to the increased electronic effects between pyridyl and polar residues. The electronic effects were also observed when mutating other residues surrounding the stereospecificity pocket of CALB, such as T42A, S47A, A281S or A281C, and can be used to manipulate the stereoselectivity. A series of bulky pyridyl(phenyl) methanols, including S-(4-chlorophenyl)(pyridin-2-yl) methanol (S-CPMA), the intermediate of bepotastine, were obtained in good yields and ee values. (Figure presented.).
- Li, Dan-Yang,Lou, Yu-Jiao,Xu, Jian,Chen, Xiao-Yang,Lin, Xian-Fu,Wu, Qi
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- Rapid and efficient acetylation of alcohols and phenols with acetic anhydride using tin(IV) porphyrin as catalyst
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The efficient and rapid esterification of alcohols and phenols in acetic anhydride was achieved by tin(IV) tetraphenylporphyrin perchlorate [SnIV (tpp) (ClO4)2] as catalyst in high yields. SnIV (tpp) (ClO4)2 showed highly catalytic activity on the acetylation reaction.
- Tangestaninejad, Shahram,Habibi, Mohammad Hossein,Mirkhani, Valiollah,Moghadam, Majid
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p. 1337 - 1343
(2007/10/03)
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- Synthesis of optically active α-phenylpyridylmethanols with Baker's yeast
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We have synthesized optically active α-phenylpyridylmethanols by using free baker's yeast (FBY) in water, immobilized baker's yeast (IMBY) in water, and IMBY in hexane.
- Takemoto,Achiwa
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p. 802 - 805
(2007/10/02)
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