共 72 条
Papain-catalyzed aldol reaction for the synthesis of trifluoromethyl carbinol derivatives
被引:15
作者:

Guo, Jun-Tao
论文数: 0 引用数: 0
h-index: 0
机构:
Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

Xiang, Yang
论文数: 0 引用数: 0
h-index: 0
机构:
Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

Guan, Zhi
论文数: 0 引用数: 0
h-index: 0
机构:
Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

He, Yan-Hong
论文数: 0 引用数: 0
h-index: 0
机构:
Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
机构:
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
基金:
中国国家自然科学基金;
关键词:
Papain;
Aldol reaction;
Trifluoromethyl carbinol derivatives;
Enzyme catalytic promiscuity;
DYNAMIC KINETIC RESOLUTION;
BOND-FORMING REACTIONS;
DIELS-ALDER REACTION;
ONE-POT SYNTHESIS;
ASYMMETRIC-SYNTHESIS;
TERTIARY ALCOHOLS;
AROMATIC KETONES;
PRIMARY AMINE;
ENANTIOSELECTIVE SYNTHESIS;
ORGANIC-SYNTHESIS;
D O I:
10.1016/j.molcatb.2016.05.014
中图分类号:
Q5 [生物化学];
Q7 [分子生物学];
学科分类号:
071010 ;
081704 ;
摘要:
Papain from Carica papaya demonstrated catalytic promiscuity was first discovered to catalyze the synthesis of trifluoromethyl carbinol derivatives via aldol reaction between alpha,alpha,alpha-trifluoromethyl ketones and aliphatic ketones in a mixed solvent of DMF and water. The best results of the corresponding aldol products with up to 99% yield and 30% ee were achieved. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:55 / 64
页数:10
相关论文
共 72 条
[1]
Catalytic Enantioselective Aldol Additions to Ketones
[J].
Adachi, Shinya
;
Harada, Toshiro
.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,
2009, 2009 (22)
:3661-3671

Adachi, Shinya
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

Harada, Toshiro
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan
[2]
Lipase-catalyzed domino dynamic kinetic resolution of racemic 3-vinylcyclohex-2-en-1-ols/intramolecular Diels-Alder reaction: One-pot synthesis of optically active polysubstituted decalins
[J].
Akai, S
;
Tanimoto, K
;
Kita, Y
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004, 43 (11)
:1407-1410

Akai, S
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

Tanimoto, K
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

Kita, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
[3]
What makes an enzyme promiscuous?
[J].
Babtie, Ann
;
Tokuriki, Nobuhiko
;
Hollfelder, Florian
.
CURRENT OPINION IN CHEMICAL BIOLOGY,
2010, 14 (02)
:200-207

论文数: 引用数:
h-index:
机构:

Tokuriki, Nobuhiko
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England Univ Cambridge, Dept Biochem, Cambridge CB2 1GA, England

Hollfelder, Florian
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cambridge, Dept Biochem, Cambridge CB2 1GA, England Univ Cambridge, Dept Biochem, Cambridge CB2 1GA, England
[4]
Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride
[J].
Bejot, R
;
Tisserand, S
;
Reddy, LM
;
Barma, DK
;
Baati, R
;
Falck, JR
;
Mioskowski, C
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005, 44 (13)
:2008-2011

Bejot, R
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Tisserand, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Reddy, LM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Barma, DK
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Baati, R
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Falck, JR
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

Mioskowski, C
论文数: 0 引用数: 0
h-index: 0
机构: Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA
[5]
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

Branneby, C
论文数: 0 引用数: 0
h-index: 0
机构: AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden

Carlqvist, P
论文数: 0 引用数: 0
h-index: 0
机构: AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden

Magnusson, A
论文数: 0 引用数: 0
h-index: 0
机构: AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden

Hult, K
论文数: 0 引用数: 0
h-index: 0
机构: AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden

Brinck, T
论文数: 0 引用数: 0
h-index: 0
机构:
AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden

Berglund, P
论文数: 0 引用数: 0
h-index: 0
机构: AlbaNova Univ Ctr, KTH, Dept Biotechnol, SE-10691 Stockholm, Sweden
[6]
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

Busto, Eduardo
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain

Gotor-Fernandez, Vicente
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain

Gotor, Vicente
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
[7]
One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water
[J].
Chai, She-Jie
;
Lai, Yi-Feng
;
Xu, Jiang-Cheng
;
Zheng, Hui
;
Zhu, Qing
;
Zhang, Peng-Fei
.
ADVANCED SYNTHESIS & CATALYSIS,
2011, 353 (2-3)
:371-375

Chai, She-Jie
论文数: 0 引用数: 0
h-index: 0
机构:
Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

Lai, Yi-Feng
论文数: 0 引用数: 0
h-index: 0
机构:
Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

Xu, Jiang-Cheng
论文数: 0 引用数: 0
h-index: 0
机构:
Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

Zheng, Hui
论文数: 0 引用数: 0
h-index: 0
机构:
Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

Zhu, Qing
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ Technol, Coll Biol & Environm Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China

Zhang, Peng-Fei
论文数: 0 引用数: 0
h-index: 0
机构:
Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Zhejiang, Peoples R China
[8]
Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine
[J].
Chen, Wen-Bing
;
Du, Xi-Lin
;
Cun, Lin-Feng
;
Zhang, Xiao-Mei
;
Yuan, Wei-Cheng
.
TETRAHEDRON,
2010, 66 (07)
:1441-1446

Chen, Wen-Bing
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

Du, Xi-Lin
论文数: 0 引用数: 0
h-index: 0
机构:
Fourth Mil Med Univ, Tangdu Hosp, Dept Gen Surg, Xian 710038, Peoples R China Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

Cun, Lin-Feng
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

Zhang, Xiao-Mei
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

Yuan, Wei-Cheng
论文数: 0 引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[9]
Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
[J].
Córdova, A
;
Notz, W
;
Barbas, CF
.
JOURNAL OF ORGANIC CHEMISTRY,
2002, 67 (01)
:301-303

Córdova, A
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

Notz, W
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

Barbas, CF
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[10]
A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
[J].
COREY, EJ
;
LINK, JO
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1992, 114 (05)
:1906-1908

COREY, EJ
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge

LINK, JO
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge