Enzyme-catalyzed asymmetric construction of chiral tertiary alcohols via aldol reaction using proteinase

被引：6
作者：
Li, Rui [1 ]
Li, Zhi-Lin [1 ]
Zhou, Hai-Yan [2 ]
He, Yan-Hong [1 ]
Guan, Zhi [1 ]
机构：
[1] Southwest Univ, Key Lab Appl Chem Chongqing Municipal, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China
[2] Southwest Univ, Sch Life Sci, Chongqing 400715, Peoples R China
来源：
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2016年 / 126卷
基金：
中国国家自然科学基金;
关键词：
Proteinase from Aspergillus melleus; Asymmetric aldol reaction; Chiral tertiary alcohol; Enzymatic promiscuity; Enzyme catalysis; BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; QUATERNARY CARBON CENTERS; BOND FORMATION; BIOCATALYTIC PROMISCUITY; ALKALINE PROTEINASE; ASPERGILLUS-MELLEUS; KETONES; ADDITIONS; LIPASE; ACIDS;
D O I：
10.1016/j.molcatb.2016.01.008
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A new enzyme-catalyzed asymmetric construction of chiral tertiary alcohols via asymmetric aldol reactions between beta,gamma-unsaturated alpha-keto esters and ketones was reported. Proteinase from Aspergillus melleus (AMP) was used as a sustainable biocatalyst. The best results can be obtained with yields of up to 90%, diastereoselectives of up to 93:7 dr, and enantioselectivities of up to 70% ee. This work not only expands the application of enzymatic promiscuity, but also provides more examples for constructing chiral tertiary alcohols. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：90 / 98
页数：9
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共 58 条
  • [1] A chiral Ag-based catalyst for practical, efficient, and highly enantioselective additions of enolsilanes to α-ketoesters
    Akullian, Laura C.
    Snapper, Marc L.
    Hoveyda, Amir H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) : 6532 - 6533
  • [2] Carbon-carbon bonds by hydrolytic enzymes
    Branneby, C
    Carlqvist, P
    Magnusson, A
    Hult, K
    Brinck, T
    Berglund, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) : 874 - 875
  • [3] Trypsin-catalyzed direct asymmetric aldol reaction
    Chen, Yan-Li
    Li, Wei
    Liu, Yan
    Guan, Zhi
    He, Yan-Hong
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 87 : 83 - 87
  • [4] Recent progress in stereoselective synthesis with aldolases
    Clapes, Pere
    Fessner, Wolf-Dieter
    Sprenger, Georg A.
    Samland, Anne K.
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (02) : 154 - 167
  • [5] Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors
    Corbett, JW
    Ko, SS
    Rodgers, JD
    Gearhart, LA
    Magnus, NA
    Bacheler, LT
    Diamond, S
    Jeffrey, S
    Klabe, RM
    Cordova, BC
    Garber, S
    Logue, K
    Trainor, GL
    Anderson, PS
    Erickson-Viitanen, SK
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) : 2019 - 2030
  • [6] Arylamine-Catalyzed Enamine Formation: Cooperative Catalysis with Arylamines and Acids
    Deng, Yongming
    Liu, Lu
    Sarkisian, Ryan G.
    Wheeler, Kraig
    Wang, Hong
    Xu, Zhenghu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) : 3663 - 3667
  • [7] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
    Evans, DA
    Kozlowski, MC
    Burgey, CS
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7893 - 7894
  • [8] DISACCHARIDE MIMETICS BY ENZYMATIC TANDEM ALDOL ADDITIONS
    EYRISCH, O
    FESSNER, WD
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) : 1639 - 1641
  • [9] Biocatalytic synthesis of hydroxylated natural products using aldolases and related enzymes
    Fessner, WD
    Helaine, V
    [J]. CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (06) : 574 - 586
  • [10] Highly efficient and large-scalable glucoamylase-catalyzed Henry reactions
    Gao, Na
    Chen, Yan-Li
    He, Yan-Hong
    Guan, Zhi
    [J]. RSC ADVANCES, 2013, 3 (37): : 16850 - 16856
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