Biocatalytic asymmetric formation of tetrahydro-β-carbolines

被引：42

作者：

Bernhardt, Peter ^{[1
]}

Usera, Aimee R. ^{[1
]}

O'Connor, Sarah E. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 33期

关键词：

PICTET-SPENGLER REACTIONS; STRICTOSIDINE SYNTHASE; ALKALOID BIOSYNTHESIS; ENZYME; EXPRESSION; CATALYSIS; SEQUENCE;

D O I：

10.1016/j.tetlet.2010.06.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved

引用

页码：4400 / 4402

页数：3

共 22 条

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