Enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction for the synthesis of 1,2-dihydroquinolines using pepsin from porcine gastric mucosa

被引：8

作者：

Zhang, Xue-Dong ^{[1
]}

Gao, Na ^{[1
]}

Guan, Zhi ^{[1
]}

He, Yan-Hong ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2016年 / 27卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Pepsin; Biocatalysis; Domino aza-Michael/aldol reaction; 1,2-Dihydroquinolines; Enzyme catalytic promiscuity; INTRAMOLECULAR ALLYLIC AMINATION; CARBON BOND FORMATION; MANNICH REACTION; ALDOL REACTION; BIOCATALYTIC PROMISCUITY; HYDROXYNITRILE LYASE; ASPERGILLUS-MELLEUS; ORGANIC-SYNTHESIS; HENRY REACTION; DERIVATIVES;

D O I：

10.1016/j.cclet.2016.02.013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented enzyme-catalyzed asymmetric domino aza-Michaelialdol reaction of 2-aminobenzaldehyde and alpha,beta-unsaturated aldehydes is achieved. Pepsin from porcine gastric mucosa provided mild and efficient access to diverse substituted 1,2-dihydroquinolines in yields of 38%-97% with 6%-24% enantiomeric excess (ee). This work not only provides a novel method for the synthesis of dihydroquinoline derivatives, but also promotes the development of enzyme catalytic promiscuity. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

收藏

页码：964 / 968

页数：5

相关论文

共 53 条

[1] The 'evolvability' of promiscuous protein functions [J].

Aharoni, A ;

Gaidukov, L ;

Khersonsky, O ;

Gould, SM ;

Roodveldt, C ;

Tawfik, DS .

NATURE GENETICS, 2005, 37 (01) :73-76

[2] NOVEL, POTENT, AND SELECTIVE 5-HT3 RECEPTOR ANTAGONISTS BASED ON THE ARYLPIPERAZINE SKELETON - SYNTHESIS, STRUCTURE, BIOLOGICAL-ACTIVITY, AND COMPARATIVE MOLECULAR-FIELD ANALYSIS STUDIES [J].

ANZINI, M ;

CAPPELLI, A ;

VOMERO, S ;

GIORGI, G ;

LANGER, T ;

HAMON, M ;

MERAHI, N ;

EMERIT, BM ;

CAGNOTTO, A ;

SKORUPSKA, M ;

MENNINI, T ;

PINTO, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2692-2704

[3] [1,5]-hydride transfer/cyclizations on alkynyl Fischer carbene complexes:: Synthesis of 1,2-dihydroquinolinyl carbene complexes and cascade reactions [J].

Barluenga, Jose ;

Fananas-Mastral, Martin ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6594-6597

[4] Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines [J].

Bhanja, Chittaranjan ;

Jena, Satyaban ;

Nayak, Sabita ;

Mohapatra, Seetaram .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1668-1694

[5] Dihydroquinoline Carbamate Derivatives as "Bio-oxidizable" Prodrugs for Brain Delivery of Acetylcholinesterase Inhibitors: [11C] Radiosynthesis and Biological Evaluation [J].

Bohn, Pierre ;

Gourand, Fabienne ;

Papamicael, Cyril ;

Ibazizene, Meziane ;

Dhilly, Martine ;

Gembus, Vincent ;

Aix, Florent ;

Tintas, Mihaela-Liliana ;

Marsais, Francis ;

Barre, Louisa ;

Levacher, Vincent .

ACS CHEMICAL NEUROSCIENCE, 2015, 6 (05) :737-744

[6] Carbon-carbon bonds by hydrolytic enzymes [J].

Branneby, C ;

Carlqvist, P ;

Magnusson, A ;

Hult, K ;

Brinck, T ;

Berglund, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :874-875

[7] EFFECT OF 6-ETHOXY 2,2,4-TRIMETHYL-1,2-DIHYDROQUINOLINE (ETHOXYQUIN) ON CARBON-TETRACHLORIDE METABOLISM IN RAT [J].

CAWTHORNE, MA ;

PALMER, ED ;

GREEN, J .

BIOCHEMICAL PHARMACOLOGY, 1973, 22 (07) :783-788

[8] A Novel Trypsin-Catalyzed Three-Component Mannich Reaction [J].

Chai, She-Jie ;

Lai, Yi-Feng ;

Zheng, Hui ;

Zhang, Peng-Fei .

HELVETICA CHIMICA ACTA, 2010, 93 (11) :2231-2236

[9] X-RAY ANALYSES OF ASPARTIC PROTEINASES .2. 3-DIMENSIONAL STRUCTURE OF THE HEXAGONAL CRYSTAL FORM OF PORCINE PEPSIN AT 2.3-A RESOLUTION [J].

COOPER, JB ;

KHAN, G ;

TAYLOR, G ;

TICKLE, IJ ;

BLUNDELL, TL .

JOURNAL OF MOLECULAR BIOLOGY, 1990, 214 (01) :199-222

[10]

Couladouros EA, 2002, ANGEW CHEM INT EDIT, V41, P3677, DOI 10.1002/1521-3773(20021004)41:19<3677::AID-ANIE3677>3.0.CO

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