Transaminase-Catalyzed Racemization with Potential for Dynamic Kinetic Resolutions

被引:12
作者
Ruggieri, Federica [1 ,2 ]
van Langen, Luuk M. [3 ]
Logan, Derek T. [2 ]
Walse, Bjorn [2 ]
Berglund, Per [1 ]
机构
[1] AlbaNova Univ Ctr, KTH Royal Inst Technol, Dept Ind Biotechnol, SE-10691 Stockholm, Sweden
[2] SARom Biostruct AB, SE-22381 Lund, Sweden
[3] Viazym BV, NL-2629 JD Delft, Netherlands
关键词
Chiral amines; Enzyme catalysis; Racemization; Transaminase; CHIRAL AMINES; ASYMMETRIC-SYNTHESIS; OMEGA-TRANSAMINASE; PYRUVATE DECARBOXYLASE; RANEY-NICKEL; EFFICIENT; PALLADIUM; ALCOHOLS; LIPASE;
D O I
10.1002/cctc.201801049
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Dynamic kinetic resolution (DKR) reactions in which a stereoselective enzyme and a racemization step are coupled in one pot would represent powerful tools for the production of enantiopure amines through enantioconvergence of racemates. The exploitation of DKR strategies is currently hampered by the lack of effective, enzyme-compatible and scalable racemization strategies for amines. In the present work, the proof of concept of a fully biocatalytic method for amine racemization is presented. Both enantiomers of the model compound 1-methyl-3-phenylpropylamine could be racemized in water and at room temperature using a couple of wild-type, non-proprietary, enantiocomplementary amine transaminases and a minimum amount of pyruvate/alanine as a co-substrate couple. The biocatalytic simultaneous parallel cascade reaction presented here poses itself as a customizable amine racemization system with potential for the chemical industry in competition with traditional transition-metal catalysis.
引用
收藏
页码:5026 / 5032
页数:7
相关论文
共 54 条
  • [31] ω-Transaminases for the synthesis of non-racemic α-chiral primary amines
    Koszelewski, Dominik
    Tauber, Katharina
    Faber, Kurt
    Kroutil, Wolfgang
    [J]. TRENDS IN BIOTECHNOLOGY, 2010, 28 (06) : 324 - 332
  • [32] Dynamic kinetic resolution catalyzed by enzymes and metals
    Martin-Matute, Belen
    Backvall, Jan-E
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2007, 11 (02) : 226 - 232
  • [33] Evolution of titanium(IV) alkoxides and Raney nickel for asymmetric reductive amination of prochiral aliphatic ketones
    Nugent, TC
    Wakchaure, VN
    Ghosh, AK
    Mohanty, RR
    [J]. ORGANIC LETTERS, 2005, 7 (22) : 4967 - 4970
  • [34] Chemoenzymatic dynamic kinetic resolution of primary amines
    Paetzold, J
    Bäckvall, JE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) : 17620 - 17621
  • [35] An efficient and mild ruthenium-catalyzed racemization of amines:: application to the synthesis of enantiomerically pure amines
    Pàmies, O
    Éll, AH
    Samec, JSM
    Hermanns, N
    Bäckvall, JE
    [J]. TETRAHEDRON LETTERS, 2002, 43 (26) : 4699 - 4702
  • [36] One-Pot Conversion of L-Threonine into L-Homoalanine: Biocatalytic Production of an Unnatural Amino Acid from a Natural One
    Park, Eulsoo
    Kim, Minji
    Shin, Jong-Shik
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3391 - 3398
  • [37] Heterogeneous Raney nickel and cobalt catalysts for racemization and dynamic kinetic resolution of amines
    Parvulescu, Andrei N.
    Jacobs, Pierre A.
    De Vos, Dirk E.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) : 113 - 121
  • [38] Palladium catalysts on alkaline-earth supports for racemization and dynamic kinetic resolution of benzylic amines
    Parvulescu, Andrei N.
    Jacobs, Pierre A.
    De Vos, Dirk E.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) : 2034 - 2043
  • [39] Cloning and characterization of the Zymobacter palmae pyruvate decarboxylase gene (pdc) and comparison to bacterial homologues
    Raj, KC
    Talarico, LA
    Ingram, LO
    Maupin-Furlow, JA
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2002, 68 (06) : 2869 - 2876
  • [40] Reetz MT, 1996, CHIMIA, V50, P668