Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis

被引：14

作者：

Guisado-Barrios, Gregorio ^{[1
]}

Munoz, Bianca K. ^{[1
]}

Kamer, Paul C. J. ^{[1
]}

Lastdrager, Bas ^{[2
]}

van der Marel, Gijs ^{[2
]}

Overhand, Mark ^{[2
]}

Vega-Vazquez, Marino ^{[3
]}

Martin-Pastor, Manuel ^{[3
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

[2] Leiden Inst Sci, Fac Sci, NL-2333 CC Leiden, Netherlands

[3] Univ Santiago de Compostela, Lab Integral Dinam & Estruct Biomol Jose R Carrac, Unidade Resonancia Magnet, RIAIDT, Santiago De Compostela 15706, Spain

来源：

DALTON TRANSACTIONS | 2013年 / 42卷 / 06期

关键词：

ARTIFICIAL METALLOENZYMES; DIRECTED EVOLUTION; ALLYLIC ALKYLATION; HYDROGENATION; ENZYMES; ENANTIOSELECTIVITY; LIBRARIES; ACID;

D O I：

10.1039/c2dt31782f

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cyclic peptide gramicidin S was used as a rigid template to provide novel peptide-based bisphosphine ligands for transition metal catalysis. Two bisphosphine-coordinated Rh(I) complexes allowed asymmetric hydrogenation with 10-52% ee and the corresponding Pd(II) analogues catalysed asymmetric allylic alkylation with 13-15% ee.

引用

页码：1973 / 1978

页数：6

共 50 条

[1] P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis
Colby, EA
Jamison, TF
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01): : 156 - 166
[2] Asymmetric catalysis with chiral phosphines containing aromatic backbones
Zhang, XM
Longmire, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U463 - U463
[3] Chiral Allene-Containing Phosphines in Asymmetric Catalysis
Cai, Feng
Pu, Xiaotao
Qi, Xiangbing
Lynch, Vincent
Radha, Akella
Ready, Joseph M.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) : 18066 - 18069
[4] Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis
Bures, Filip
Szotkowski, Tomd
Kulhánek, Jirí
Pytela, Oldrich
Ludwig, Miroslav
Holcapek, Michal
TETRAHEDRON-ASYMMETRY, 2006, 17 (06) : 900 - 907
[5] Novel, practical ligands for asymmetric catalysis
不详
CHIMICA OGGI-CHEMISTRY TODAY, 2002, 20 (10) : 33 - 33
[6] Phosphite-Containing Ligands for Asymmetric Catalysis
van Leeuwen, Piet W. N. M.
Kamer, Paul C. J.
Claver, Carmen
Pamies, Oscar
Dieguez, Montserrat
CHEMICAL REVIEWS, 2011, 111 (03) : 2077 - 2118
[7] Molecular dynamics simulation of the cyclic decapeptide antibiotic, gramicidin S, in dimethyl sulfoxide solution
Mihailescu, D
Smith, JC
JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (09): : 1586 - 1594
[8] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS
ALLEN, JV
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
COOTE, SJ
TETRAHEDRON, 1994, 50 (03) : 799 - 808
[9] PURIFICATION AND CHARACTERIZATION OF A NEW METAL PROTEASE WHICH HYDROLYZES THE CYCLIC DECAPEPTIDE, GRAMICIDIN-S
MAEDA, T
TAKAGI, M
IMANAKA, T
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1993, 75 (03): : 173 - 177
[10] Reinventing phenanthroline ligands - Chiral derivatives for asymmetric catalysis?
Schoffers, E
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (07) : 1145 - 1152

← 1 2 3 4 5 →