Classification and functional origins of stereocomplementary alcohol dehydrogenases for asymmetric synthesis of chiral secondary alcohols: A review

被引:7
|
作者
Zhang, Lu [1 ]
Sun, Zewen [1 ]
Xu, Guochao [1 ]
Ni, Ye [1 ]
机构
[1] Jiangnan Univ, Sch Biotechnol, Key Lab Ind Biotechnol, Minist Educ, Wuxi 214122, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Alcohol dehydrogenase; Stereocomplementary; Catalytic mechanism; TROPINONE REDUCTASE-II; ALDO-KETO REDUCTASES; SHORT-CHAIN DEHYDROGENASE/REDUCTASE; CARBONYL REDUCTASE; SUBSTRATE-BINDING; SPOROBOLOMYCES-SALMONICOLOR; ENANTIOSELECTIVE REDUCTION; CHEMOENZYMATIC SYNTHESIS; SATURATION MUTAGENESIS; STRUCTURAL INSIGHTS;
D O I
10.1016/j.ijbiomac.2024.132238
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
Alcohol dehydrogenases (ADHs) mediated biocatalytic asymmetric reduction of ketones have been widely applied in the synthesis of optically active secondary alcohols with highly reactive hydroxyl groups ligated to the stereogenic carbon and divided into (R)- and (S)-configurations. Stereocomplementary ADHs could be applied in the synthesis of both enantiomers and are increasingly accepted as the "first of choice" in green chemistry due to the high atomic economy, low environmental factor, 100 % theoretical yield, and high environmentally friendliness. Due to the equal importance of complementary alcohols, development of stereocomplementary ADHs draws increasing attention. This review is committed to summarize recent advance in discovery of naturally evolved and tailor-made stereocomplementary ADHs, unveil the molecular mechanism of stereoselective catalysis in views of classification and functional basis, and provide guidance for further engineering the stereoselectivity of ADHs for the industrial biosynthesis of chiral secondary alcohol of industrial relevance.
引用
收藏
页数:13
相关论文
共 50 条
  • [1] Stereocomplementary asymmetric bioreduction of boron-containing ketones mediated by alcohol dehydrogenases
    Barcellos, Thiago
    Tauber, Katharina
    Kroutil, Wolfgang
    Andrade, Leandro H.
    TETRAHEDRON-ASYMMETRY, 2011, 22 (18-19) : 1772 - 1777
  • [2] STEREOSPECIFIC OXIDATION OF SECONDARY ALCOHOLS BY HUMAN ALCOHOL DEHYDROGENASES
    STONE, CL
    LI, TK
    BOSRON, WF
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1989, 264 (19) : 11112 - 11116
  • [3] CATALYTIC ASYMMETRIC - SYNTHESIS OF CHIRAL SECONDARY POLYFUNCTIONAL ALCOHOLS USING DIORGANOZINCS
    KNOCHEL, P
    VETTEL, S
    EISENBERG, C
    APPLIED ORGANOMETALLIC CHEMISTRY, 1995, 9 (03) : 175 - 188
  • [4] New Alcohol Dehydrogenases for the Synthesis of Chiral Compounds
    Hummel, W.
    Advances in Biochemical Engineering - Biotechnology, (58):
  • [5] Synthesis of Chiral Secondary β-amino Alcohols and their Application in the Asymmetric Reduction of Prochiral Ketones
    Ran, De-Qiang
    Shen, Tian-Hua
    Zhou, Xiao-Cong
    Ma, Chun-An
    Song, Qing-Bao
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2013, 35 (01): : 125 - 129
  • [6] Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols
    Bai, Dongya
    He, Junyao
    Ouyang, Bin
    Huang, Jin
    Wang, Pu
    PROGRESS IN CHEMISTRY, 2017, 29 (05) : 491 - 501
  • [7] Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases
    Chen, Fei-Fei
    Cosgrove, Sebastian C.
    Birmingham, William R.
    Mangas-Sanchez, Juan
    Citoler, Joan
    Thompson, Matthew P.
    Zheng, Gao-Wei
    Xu, Jian-He
    Turner, Nicholas J.
    ACS CATALYSIS, 2019, 9 (12): : 11813 - 11818
  • [8] Microbial alcohol dehydrogenases: recent developments and applications in asymmetric synthesis
    Chadha, Anju
    Padhi, Santosh Kumar
    Stella, Selvaraj
    Venkataraman, Sowmyalakshmi
    Saravanan, Thangavelu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (02) : 228 - 251
  • [9] SYNTHESIS OF CHIRAL ALCOHOLS USING STABLE SEC-ALCOHOL DEHYDROGENASES IN A SUBSTRATE-COUPLED COFACTOR RECYCLE SYSTEM
    PLANT, AR
    COWAN, DA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 99 - BIOT
  • [10] Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols
    Kondo, Yui
    Nagao, Kazunori
    Ohmiya, Hirohisa
    CHEMICAL COMMUNICATIONS, 2020, 56 (54) : 7471 - 7474