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

被引：111

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 35期

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.

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收藏

页码：6707 / 6711

页数：5

相关论文

共 54 条

[31] Synthesis of β-cyclopropylalanines by photolysis of diacyl peroxides [J].

Jain, RP ;

Vederas, JC .

ORGANIC LETTERS, 2003, 5 (24) :4669-4672

[32]

Johnson R.A, 1991, Comp. Org. Synth, V7, P389

[33] Oligopeptides as catalysts for asymmetric epoxidation [J].

Kelly, DR ;

Roberts, SM .

BIOPOLYMERS, 2006, 84 (01) :74-89

[34] ENZYME CATALYSIS - NOT DIFFERENT, JUST BETTER [J].

KNOWLES, JR .

NATURE, 1991, 350 (6314) :121-124

[35] STERIC CONTROL OF EPOXIDATION BY CARBAMATE AND AMIDE GROUPS - EVIDENCE FOR THE CARBONYL-DIRECTED EPOXIDATION [J].

KOCOVSKY, P ;

STARY, I .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3236-3243

[36] Enantioselective organocatalytic epoxidation using hypervalent iodine reagents [J].

Lee, Sandra ;

MacMillan, David W. C. .

TETRAHEDRON, 2006, 62 (49) :11413-11424

[37] Molecular mechanics parameters and conformational free energies of proline-containing peptides [J].

McDonald, DQ ;

Still, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1385-1391

[38] Stabilization of α-helices by dipole-dipole interactions within α-helices [J].

Park, C ;

Goddard, WA .

JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (32) :7784-7789

[39] Aspartate-catalyzed asymmetric epoxidation reactions [J].

Peris, Gorka ;

Jakobsche, Charles E. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) :8710-+

[40] NEW OXIDIZING-AGENTS FROM THE DEHYDRATION OF HYDROGEN-PEROXIDE [J].

REBEK, J ;

MCCREADY, R ;

WOLF, S ;

MOSSMAN, A .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1485-1493

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