Enantioselective Artificial Metalloenzymes Based on a Bovine Pancreatic Polypeptide Scaffold

被引:78
作者
Coquiere, David [1 ]
Bos, Jeffrey [1 ]
Beld, Joris [2 ]
Roelfes, Gerard [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
[2] ETH, Organ Chem Lab, Honggerberg HCI, CH-8093 Zurich, Switzerland
关键词
artificial metalloenzymes; asymmetric catalysis; copper; Diels-Alder reactions; Michael addition; ALPHA; BETA-UNSATURATED 2-ACYL IMIDAZOLES; ASYMMETRIC CATALYSIS; OXALOACETATE DECARBOXYLASE; TRIFLATE COMPLEXES; DIRECTED EVOLUTION; HYBRID CATALYSTS; BIOTIN-AVIDIN; DESIGN; PROTEIN; PEPTIDE;
D O I
10.1002/anie.200901134
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Site creation: Enantioselective artificial metalloenzymes have been created by grafting a new active site onto bovine pancreatic polypeptide through the introduction of an amino acid capable of coordinating a copper(II) ion. This hybrid catalyst gave good enantioselectivities in the Diels- Alder and Michael addition reactions in water (see scheme) and displayed a very high substrate selectivity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5159 / 5162
页数:4
相关论文
共 44 条
[1]   Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design [J].
Agarkov, A ;
Greenfield, S ;
Xie, DJ ;
Pawlick, R ;
Starkey, G ;
Gilbertson, SR .
BIOPOLYMERS, 2006, 84 (01) :48-73
[2]  
Barany G., 1979, The Peptides, V2, P1
[3]   Biophysical methods to study ligand-receptor interactions of neuropeptide Y [J].
Beck-Sickinger, AG .
BIOPOLYMERS, 2001, 60 (06) :420-437
[4]   COMPLETE L-ALANINE SCAN OF NEUROPEPTIDE-Y REVEALS LIGANDS BINDING TO Y-1 AND Y-2 RECEPTORS WITH DISTINGUISHED CONFORMATIONS [J].
BECKSICKINGER, AG ;
WIELAND, HA ;
WITTNEBEN, H ;
WILLIM, KD ;
RUDOLF, K ;
JUNG, G .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1994, 225 (03) :947-958
[5]   ON THE TENDENCY OF THE METAL IONS TOWARD COMPLEX FORMATION [J].
BJERRUM, J .
CHEMICAL REVIEWS, 1950, 46 (02) :381-401
[6]   X-RAY-ANALYSIS (1.4-A RESOLUTION) OF AVIAN PANCREATIC-POLYPEPTIDE - SMALL GLOBULAR PROTEIN HORMONE [J].
BLUNDELL, TL ;
PITTS, JE ;
TICKLE, IJ ;
WOOD, SP ;
WU, CW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (07) :4175-4179
[7]   DNA-based asymmetric catalysis: Sequence-dependent rate acceleration and enantioselectivity [J].
Boersma, Arnold J. ;
Klijn, Jaap E. ;
Feringa, Ben L. ;
Roelfes, Gerard .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (35) :11783-11790
[8]   α,β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water [J].
Boersma, Arnold J. ;
Feringa, Ben L. ;
Roelfes, Gerard .
ORGANIC LETTERS, 2007, 9 (18) :3647-3650
[9]   A site-selective dual anchoring strategy for artificial metalloprotein design [J].
Carey, JR ;
Ma, SK ;
Pfister, TD ;
Garner, DK ;
Kim, HK ;
Abramite, JA ;
Wang, ZL ;
Guo, ZJ ;
Lu, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10812-10813
[10]   Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries [J].
Christensen, Christian A. ;
Meldal, Morten .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01) :79-85