The L-Leu Hexamer, a Short and Highly Enantioselective Peptide Catalyst for the Julia-Colonna Epoxidation: Stabilization of a Helical Conformation in DMSO

被引:24
作者
Weyer, Alexandra [1 ]
Diaz, Dolores [2 ]
Nierth, Alexander [1 ]
Schloerer, Nils E. [1 ]
Berkessel, Albrecht [1 ]
机构
[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany
[2] CSIC, Dept Biol Fisicoquim, Ctr Invest Biol, E-28040 Madrid, Spain
关键词
enantioselectivity; epoxidation; molecular dynamics; NMR spectroscopy; organocatalysis; PHASE-BOUND PEPTIDES; ENONE EPOXIDATION; DYNAMICS; OLIGOPEPTIDES; PROTEINS; PROGRAM;
D O I
10.1002/cctc.201100243
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:337 / 340
页数:4
相关论文
共 41 条
[1]  
[Anonymous], DISC STUD MOD ENV RE
[2]  
[Anonymous], 1986, NMR of proteins and nucleic acids
[3]   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
[4]   Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: Dominant role of peptide helicity [J].
Berkessel, A ;
Gasch, N ;
Glaubitz, K ;
Koch, C .
ORGANIC LETTERS, 2001, 3 (24) :3839-3842
[5]   Enantioselective aldol reaction catalysed by polyleucines [J].
Carrea, Giacomo ;
Ottolina, Gianluca ;
Lazcano, Antonio ;
Pironti, Vincenza ;
Colonna, Stefano .
TETRAHEDRON-ASYMMETRY, 2007, 18 (11) :1265-1268
[6]  
Case D.A., 2004, AMBER 8
[7]   Enantioselective reactions catalyzed by synthetic enzymes. A model for chemical evolution [J].
Colonna, Stefano ;
Perdicchia, Dario ;
Di Mauro, Ernesto .
TETRAHEDRON-ASYMMETRY, 2009, 20 (15) :1709-1714
[8]   Asymmetric catalysis mediated by synthetic peptides [J].
Davie, Elizabeth A. Colby ;
Mennen, Steven M. ;
Xu, Yingju ;
Miller, Scott J. .
CHEMICAL REVIEWS, 2007, 107 (12) :5759-5812
[9]   Structure-selectivity relationships and structure for a peptide-based enantioselective acylation catalyst [J].
Fierman, MB ;
O'Leary, DJ ;
Steinmetz, WE ;
Miller, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (22) :6967-6971
[10]   Efficient asymmetric epoxidation of α,β-unsaturated ketones using a soluble triblock polyethylene glycol-polyamino acid catalyst [J].
Flood, RW ;
Geller, TP ;
Petty, SA ;
Roberts, SM ;
Skidmore, J ;
Volk, M .
ORGANIC LETTERS, 2001, 3 (05) :683-686