Asymmetric acyloin condensation catalyzed by phenylpyruvate decarboxylase

被引:25
作者
Guo, ZW [1 ]
Goswami, A [1 ]
Mirfakhrae, KD [1 ]
Patel, RN [1 ]
机构
[1] Bristol Myers Squibb, Pharmaceut Res Inst, Proc Res & Dev, Proc Res,Enzyme Technol, New Brunswick, NJ 08903 USA
关键词
D O I
10.1016/S0957-4166(99)00548-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cells obtained from growth of Achromobacter eurydice, Pseudomonas aromatica and Pseudomonas putida on L-phenylalanine containing medium catalyzed the enzymatic acyloin condensation of phenylpyruvic acid 1 and acetardehyde 2 by phenylpyruvate decarboxylase to produce 3-hydroxy-1-phenyl-2-butanone 3. The acyloin condensation by Achramobacter eurydice and P. aromatica was stereoselective, providing the 3R enantiomer 3a with enantiomeric excess (ee) of 95% and 84%, respectively. A partially purified enzyme was prepared from the cell free extract of Achromobacter eyrydice. The acyloin product 3a was obtained in 45% yield with an ee of 91% by using this partially purified preparation of phenylpyruvate decarboxylase. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
引用
收藏
页码:4667 / 4675
页数:9
相关论文
共 50 条
[41]   STUDIES ON PYRUVATE DECARBOXYLASE - ACYLOIN FORMATION FROM ALIPHATIC, AROMATIC AND HETEROCYCLIC ALDEHYDES [J].
CROUT, DHG ;
DALTON, H ;
HUTCHINSON, DW ;
MIYAGOSHI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1329-1334
[42]   ACYLOIN CONDENSATION .1. SYNTHESES OF 1,6-DIPHENYLCYCLOPENTANONE [J].
TOTTON, EL ;
POWELL, H ;
FREEMAN, RC ;
YARBORO, TL .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (02) :343-&
[43]   ACYLOIN CONDENSATION .3. SYNTHESIS OF 4-MEMBERED RINGS [J].
BLOOMFIELD, JJ .
TETRAHEDRON LETTERS, 1968, (05) :587-+
[44]   Arylmalonate Decarboxylase-Catalyzed Asymmetric Synthesis of Both Enantiomers of Optically Pure Flurbiprofen [J].
Gassmeyer, Sarah Katharina ;
Wetzig, Jasmin ;
Muegge, Carolin ;
Assmann, Miriam ;
Enoki, Junichi ;
Hilterhaus, Lutz ;
Zuhse, Ralf ;
Miyamoto, Kenji ;
Liese, Andreas ;
Kourist, Robert .
CHEMCATCHEM, 2016, 8 (05) :916-921
[45]   Direct asymmetric aldol condensation catalyzed by aziridine semicarbazide zinc(II) complexes [J].
Pieczonka, Adam M. ;
Lesniak, Stanislaw ;
Rachwalski, Michal .
TETRAHEDRON LETTERS, 2014, 55 (15) :2373-2375
[46]   Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions [J].
Arai, S ;
Shioiri, T .
TETRAHEDRON LETTERS, 1998, 39 (15) :2145-2148
[47]   Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate [J].
Aydin, Juhanes ;
Ryden, Andreas ;
Szabo, Kalman J. .
TETRAHEDRON-ASYMMETRY, 2008, 19 (15) :1867-1870
[48]   Zinc(II) mediated asymmetric aldol condensation catalyzed by chiral aziridine ligands [J].
Pieczonka, Adam M. ;
Jarzynski, Szymon ;
Wujkowska, Zuzanna ;
Lesniak, Stanislaw ;
Rachwalski, Michal .
TETRAHEDRON LETTERS, 2015, 56 (46) :6506-6507
[49]   A NOVEL ROUTE TO THE TRIPHENYLENE RING-SYSTEM BY A TRIPLE INTRAMOLECULAR ACYLOIN CONDENSATION [J].
PRAEFCKE, K ;
PSARAS, P ;
BILGIN, B .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (01) :285-286
[50]   4-MEMBERED RINGS BY ACYLOIN CONDENSATION . A PECULIAR RESULT IN LIQUID AMMONIA [J].
BLOOMFIELD, JJ ;
IRELAN, JRS .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (06) :2017-+