A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A

被引:72
作者
Bailey, Kevin R. [1 ]
Ellis, Andrew J. [1 ]
Reiss, Renate [1 ]
Snape, Timothy J. [1 ]
Turner, Nicholas J. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester Interdisciplinary Bioctr, Manchester M1 7DN, Lancs, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1039/b710456a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A template-based mnemonic has been developed for the enzyme monoamine oxidase from Aspergillus niger and has been used to successfully identify the alkaloid (+/-)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)-enantiomer in 97% e.e.
引用
收藏
页码:3640 / 3642
页数:3
相关论文
共 18 条
[1]  
Alexeeva M, 2002, ANGEW CHEM INT EDIT, V41, P3177, DOI 10.1002/1521-3773(20020902)41:17<3177::AID-ANIE3177>3.0.CO
[2]  
2-P
[3]   SYNTHESES OF 7,8-BENZOPYRROCOLINE DERIVATIVES - A NOVEL REACTION OF REISSERT COMPOUNDS [J].
BOEKELHEIDE, V ;
GODFREY, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3679-3685
[4]  
BREMNER JB, 1985, HETEROCYCLES, V23, P1451
[5]   PHOTOSOLVOLYSIS OF BRIDGEHEAD QUATERNARY AMMONIUM-SALTS .1. SYNTHESIS OF SOME 3-BENZAZONINE DERIVATIVES [J].
BREMNER, JB ;
WINZENBERG, KN .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (06) :1203-1215
[6]   Directed evolution of an amine oxidase for the preparative deracemisation of cyclic secondary amines [J].
Carr, R ;
Alexeeva, M ;
Dawson, MJ ;
Gotor-Fernández, V ;
Humphrey, CE ;
Turner, NJ .
CHEMBIOCHEM, 2005, 6 (04) :637-639
[7]   Directed evolution of an amine oxidase possessing both broad substrate specificity and high enantioselectivity [J].
Carr, R ;
Alexeeva, M ;
Enright, A ;
Eve, TSC ;
Dawson, MJ ;
Turner, NJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) :4807-4810
[8]   l-w-halogenoalkylisoquinolines and their derivatives [J].
Child, R ;
Pyman, FL .
JOURNAL OF THE CHEMICAL SOCIETY, 1931, :36-49
[9]   A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines [J].
Dunsmore, CJ ;
Carr, R ;
Fleming, T ;
Turner, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2224-2225
[10]   A facile three-step synthesis of (±)-crispine A via an acyliminium ion cyclisation [J].
King, Frank D. .
TETRAHEDRON, 2007, 63 (09) :2053-2056