Enzymatic synthesis of L-norephedrine by coupling recombinant pyruvate decarboxylase and ω-transaminase

被引:25
作者
Wu, Xuri [1 ,2 ]
Fei, Mengdan [1 ,2 ]
Chen, Yong [1 ,2 ]
Wang, Zongqiang [1 ,2 ]
Chen, Yijun [1 ,2 ]
机构
[1] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Biol Chem Lab, Nanjing 210009, Jiangsu, Peoples R China
关键词
L-Norephedrine; L-Phenylacetylcarbinol; Biosynthesis; Pyruvate decarboxylase; omega-Transaminase; VIBRIO-FLUVIALIS [!text type='JS']JS[!/text]17; CHIRAL AMINES; ASYMMETRIC-SYNTHESIS; (R)-PHENYLACETYLCARBINOL PRODUCTION; L-HOMOPHENYLALANINE; KINETIC RESOLUTION; CANDIDA-UTILIS; SUBSTRATE; BIOCATALYSIS; ENANTIOMERS;
D O I
10.1007/s00253-014-5797-1
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
l-Norephedrine, a natural plant alkaloid, possesses similar activity as ephedrine and can be used as a vicinal amino alcohol for the asymmetric synthesis of a variety of optically pure compounds, including pharmaceuticals, fine chemicals, and agrochemicals. Because of the existence of two asymmetric centers, efficient synthesis of l-norephedrine has been challenging. In the present study, an R-selective pyruvate decarboxylase from Saccharomyces cerevisiae and an S-selective omega-transaminase from Vibrio fluvialis JS17 were coupled to develop a sequential process for the stereoselective biosynthesis of l-norephedrine. After systematic optimization of the reaction conditions, a green, economic, and practical biocatalytic method to prepare l-norephedrine was established to achieve de and ee values of greater than 99.5 % and a molar yield over 60 %. The present coupling approach can facilitate the development of sequential reactions by various biocatalysts.
引用
收藏
页码:7399 / 7408
页数:10
相关论文
共 39 条
  • [1] Development of an Amine Dehydrogenase for Synthesis of Chiral Amines
    Abrahamson, Michael J.
    Vazquez-Figueroa, Eduardo
    Woodall, Nicholas B.
    Moore, Jeffrey C.
    Bommarius, Andreas S.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) : 3969 - 3972
  • [2] The synthesis of vicinal amino alcohols
    Bergmeier, SC
    [J]. TETRAHEDRON, 2000, 56 (17) : 2561 - 2576
  • [3] Engineering the third wave of biocatalysis
    Bornscheuer, U. T.
    Huisman, G. W.
    Kazlauskas, R. J.
    Lutz, S.
    Moore, J. C.
    Robins, K.
    [J]. NATURE, 2012, 485 (7397) : 185 - 194
  • [4] ARYLETHANOLAMINES DERIVED FROM SALICYLAMIDE WITH ALPHA-ADRENOCEPTOR AND BETA-ADRENOCEPTOR BLOCKING ACTIVITIES - PREPARATION OF LABETALOL, ITS ENANTIOMERS, AND RELATED SALICYLAMIDES
    CLIFTON, JE
    COLLINS, I
    HALLETT, P
    HARTLEY, D
    LUNTS, LHC
    WICKS, PD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (06) : 670 - 679
  • [5] Nucleophilic chiral amines as catalysts in asymmetric synthesis
    France, S
    Guerin, DJ
    Miller, SJ
    Lectka, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2985 - 3012
  • [6] One-pot synthesis of amino-alcohols using a de-novo transketolase and β-alanine:: Pyruvate transaminase pathway in Escherichia coli
    Ingram, C. U.
    Bommer, M.
    Smith, M. E. B.
    Dalby, P. A.
    Ward, J. M.
    Hailes, H. C.
    Lye, G. J.
    [J]. BIOTECHNOLOGY AND BIOENGINEERING, 2007, 96 (03) : 559 - 569
  • [7] Experimental probing and modeling of key sorbent-solute interactions of norephedrine enantiomers with polysaccharide-based chiral stationary phases
    Kasat, Rahul B.
    Wang, Nien-Hwa Linda
    Franses, Elias I.
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2008, 1190 (1-2) : 110 - 119
  • [8] Substrate supply for effective biocatalysis
    Kim, Pei-Yi
    Pollard, David J.
    Woodley, John M.
    [J]. BIOTECHNOLOGY PROGRESS, 2007, 23 (01) : 74 - 82
  • [9] 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
  • [10] Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (-)-norephedrine synthesis
    Kreutz, OC
    Moran, PJS
    Rodrigues, JAR
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2649 - 2653