Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues

被引:108
作者
Jakobsche, Charles E. [1 ]
Peris, Gorka [1 ]
Miller, Scott J. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
asymmetric catalysis; epoxidation; fluorine; olefin isostere; peptides; peptidomimetic;
D O I
10.1002/anie.200802223
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Subtle exchange: Replacement of an amide function with alkene or fluoroalkene groups provides a new class of epoxidation catalysts (see scheme). The structure-dependent catalytic behavior of these isosteric peptides provides mechanistic insights in their mode of action. (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6707 / 6711
页数:5
相关论文
共 54 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]   In search of the energetic role of peptide hydrogen bonds [J].
Baldwin, RL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (20) :17581-17588
[3]   Significant inter- and intramolecular O-H•••FC hydrogen bonding [J].
Barbarich, TJ ;
Rithner, CD ;
Miller, SM ;
Anderson, OP ;
Strauss, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4280-4281
[4]   FLUOROALKENES AS PEPTIDE ISOSTERES - GROUND-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].
BARTLETT, PA ;
OTAKE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3107-3111
[5]   Asymmetric enone epoxidation by short solid-phase bound peptides: Further evidence for catalyst helicity and catalytic activity of individual peptide strands [J].
Berkessel, A ;
Koch, B ;
Toniolo, C ;
Rainaldi, M ;
Broxterman, QB ;
Kaptein, B .
BIOPOLYMERS, 2006, 84 (01) :90-96
[6]  
BERKESSEL A, 2008, ANGEW CHEM, V120, P3735
[7]   Asymmetric epoxidation of olefins with hydrogen peroxide - Catalysis by an aspartate-containing tripeptide [J].
Berkessel, Albrecht .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3677-3679
[8]   How good is fluorine as a hydrogen-bond acceptor in fluorinated single-walled carbon nanotubes? [J].
Bettinger, HF .
CHEMPHYSCHEM, 2005, 6 (06) :1169-1174
[9]   Asymmetric total synthesis of ent-(-)-roseophilin:: Assignment of absolute configuration [J].
Boger, DL ;
Hong, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8515-8519
[10]   SELECTIVE EPOXIDATION OF EICOSA-CIS-5,8,11,14-TETRAENOIC (ARACHIDONIC) ACID AND EICOSA-CIS-8,11,14-TRIENOIC ACID [J].
COREY, EJ ;
NIWA, H ;
FALCK, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1586-1587