Substituent Position-Controlled Stereoselectivity in Enzymatic Reduction of Diaryl- and Aryl(heteroaryl)methanones - Details

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Abstract：

We　report　here　the　discovery　of　a　novel　ketoreductase　(KRED),　named　KmCR2,　with　a　broad　substrate　spectrum　on　bioreduction　of　sterically　bulky　diaryl-　and　aryl(heteroaryl)methanones.　The　position　of　the　substituent　on　aromatic　rings　(meta　versus　para　or　ortho)　was　revealed　to　control　the　stereospecificity　of　KmCR2.　The　stereoselective　preparation　of　both　enantiomers　of　diaryl-　or　aryl(heteroaryl)methanols　using　strategically　engineered　substrates　with　a　traceless　directing　group　(bromo　group)　showcased　the　potential　application　of　this　substrate-controlled　bioreduction　reaction.　The　combined　use　of　substrate　engineering　and　protein　engineering,　was　demonstrated　to　be　a　useful　strategy　in　efficiently　improving　stereoselectivity　or　switching　stereopreference　of　enzymatic　processes.　(Figure　presented.).　©　2019　Wiley-VCH　Verlag　GmbH　&　Co.　KGaA,　Weinheim

Keyword：

Asymmetric catalysis; Diarylmethanol; Ketoreductase; Oxidoreductase; Substrate controlled stereoselectivity

Community：

[ 1 ] [Li, Z.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China
[ 2 ] [Li, Z.]Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, China
[ 3 ] [Wang, Z.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China
[ 4 ] [Wang, Z.]Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, China
[ 5 ] [Wang, Y.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China
[ 6 ] [Wu, X.]College of Chemical Engineering, Fuzhou University, 2 Xueyuan Road, Fuzhou, 350100, China
[ 7 ] [Lu, H.]State Key Laboratory of Genetic Engineering, School of Life Sciences, Fudan University, 2005 Songhu Road, Shanghai, 200438, China
[ 8 ] [Lu, H.]Shanghai Engineering Research Center of Industrial Microorganisms, 2005 Songhu Road, Shanghai, 200438, China
[ 9 ] [Huang, Z.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China
[ 10 ] [Huang, Z.]Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, China
[ 11 ] [Chen, F.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China
[ 12 ] [Chen, F.]Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, China

Reprint 's Address：

[Huang, Z.]Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, 220 Handan Road, China

Email：

huangzedu@fudan.edu.cn

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Source ：

Advanced Synthesis and Catalysis

ISSN： 1615-4150

Year： 2019

Issue： 8

Volume： 361

Page： 1859-1865

5 . 8 5 1

JCR@2019

4 . 4 0 0

JCR@2023

ESI HC Threshold：184

JCR Journal Grade：1

CAS Journal Grade：1

Cited Count：

WoS CC Cited Count：

SCOPUS Cited Count：

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 1

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