Trypsin-catalyzed tandem reaction: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones by in situ formed acetaldehyde

被引：29

作者：

Xie, Zong-Bo ^{[1
,2
]}

Wang, Na ^{[1
]}

Wu, Wan-Xia ^{[1
]}

Le, Zhang-Gao ^{[2
]}

Yu, Xiao-Qi ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] E China Inst Technol, Sch Chem Biol & Mat Sci, Fuzhou 344000, Peoples R China

来源：

JOURNAL OF BIOTECHNOLOGY | 2014年 / 170卷

基金：

中国国家自然科学基金;

关键词：

Biginelli reaction; Tandem protocol; One pot; Promiscuity; In situ; BIGINELLI REACTION; BIOCATALYTIC PROMISCUITY; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; IONIC LIQUIDS; LIPASE; SOLVENT; DERIVATIVES; ENZYMES;

D O I：

10.1016/j.jbiotec.2013.10.031

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：

A simple, mild, one-pot tandem method catalyzed by trypsin was developed for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones by the Biginelli reaction of urea, beta-dicarbonyl compounds, and in situ-formed acetaldehyde. Trypsin was found to display dual promiscuous functions to catalyze transesterification and the Biginelli reaction in sequence. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：1 / 5

页数：5

共 39 条

[1] Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways [J].

Bornscheuer, UT ;

Kazlauskas, RJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6032-6040

[2]

Borse B. N., 2012, CURR CHEM LETT, V1, P59, DOI [10.5267/j.ccl.2012.3.001, DOI 10.5267/J.CCL.2012.3.001]

[3] Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis [J].

Busto, Eduardo ;

Gotor-Fernandez, Vicente ;

Gotor, Vicente .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4504-4523

[4] Highly enantioselective organocatalytic Biginelli reaction [J].

Chen, Xiao-Hua ;

Xu, Xiao-Ying ;

Liu, Hua ;

Cun, Lin-Feng ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803

[5] Enzymes with extra talents: moonlighting functions and catalytic promiscuity [J].

Copley, SD .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (02) :265-272

[6] THE EFFICIENT SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN-2-(1H)-ONES AND THEIR SULFUR DERIVATIVES WITH H2SO4 IMMOBILIZED ON ACTIVATED CHARCOAL [J].

Dilmaghani, Karim Akbari ;

Zeynizadeh, Behzad ;

Parasajam, Hadi .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (04) :544-553

[7] One-pot three-component Biginelli-type reaction catalyzed by ionic liquids in aqueous media [J].

Fang, Dong ;

Zhang, Dai-zhen ;

Liu, Zu-liang .

MONATSHEFTE FUR CHEMIE, 2010, 141 (04) :419-423

[8] Efficient synthesis of 3,4-dihydropyrimidin-2-ones in low melting tartaric acid-urea mixtures [J].

Gore, Sangram ;

Baskaran, Sundarababu ;

Koenig, Burkhard .

GREEN CHEMISTRY, 2011, 13 (04) :1009-1013

[9] One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Acidic Ionic Liquids Under Solvent-Free Conditions [J].

Gui, Jianzhou ;

Liu, Dan ;

Wang, Chan ;

Lu, Feng ;

Lian, Jingzhao ;

Jiang, Heng ;

Sun, Zhaolin .

SYNTHETIC COMMUNICATIONS, 2009, 39 (19) :3436-3443

[10] BrOnsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot, Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free Conditions [J].

Hajipour, Abdol R. ;

Ghayeb, Yosof ;

Sheikhan, Nafisehsadat ;

Ruoho, Arnold E. .

SYNTHETIC COMMUNICATIONS, 2011, 41 (15) :2226-2233

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