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Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues
被引:108
作者
:
Jakobsche, Charles E.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Jakobsche, Charles E.
[
1
]
Peris, Gorka
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Peris, Gorka
[
1
]
Miller, Scott J.
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
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.
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
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h-index:
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Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Aggarwal, VK
;
Winn, CL
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0
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Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
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Stanford Univ, Beckman Ctr, Sch Med, Dept Biochem, Stanford, CA 94305 USA
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
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;
Rithner, CD
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
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;
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Miller, SM
;
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Anderson, OP
;
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
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TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
BARTLETT, PA
;
OTAKE, A
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TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
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Asymmetric enone epoxidation by short solid-phase bound peptides: Further evidence for catalyst helicity and catalytic activity of individual peptide strands
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Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
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Koch, B
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Rainaldi, M
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Broxterman, QB
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Asymmetric epoxidation of olefins with hydrogen peroxide - Catalysis by an aspartate-containing tripeptide
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Univ Cologne, Dept Chem, D-50939 Cologne, Germany
Univ Cologne, Dept Chem, D-50939 Cologne, Germany
Berkessel, Albrecht
.
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How good is fluorine as a hydrogen-bond acceptor in fluorinated single-walled carbon nanotubes?
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Ruhr Univ Bochum, Lehrstuhl Organ Chem 2, D-44780 Bochum, Germany
Bettinger, HF
.
CHEMPHYSCHEM,
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Asymmetric total synthesis of ent-(-)-roseophilin:: Assignment of absolute configuration
[J].
Boger, DL
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.
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←
1
2
3
4
5
6
→
共 54 条
[1]
Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis
[J].
Aggarwal, VK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Aggarwal, VK
;
Winn, CL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
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
论文数:
0
引用数:
0
h-index:
0
机构:
Stanford Univ, Beckman Ctr, Sch Med, Dept Biochem, Stanford, CA 94305 USA
Stanford Univ, Beckman Ctr, Sch Med, Dept Biochem, Stanford, CA 94305 USA
Baldwin, RL
.
JOURNAL OF BIOLOGICAL CHEMISTRY,
2003,
278
(20)
:17581
-17588
[3]
Significant inter- and intramolecular O-H•••FC hydrogen bonding
[J].
Barbarich, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Barbarich, TJ
;
Rithner, CD
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Rithner, CD
;
Miller, SM
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Miller, SM
;
Anderson, OP
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Anderson, OP
;
Strauss, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
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
论文数:
0
引用数:
0
h-index:
0
机构:
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
BARTLETT, PA
;
OTAKE, A
论文数:
0
引用数:
0
h-index:
0
机构:
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
TORAY INDUSTRIES LTD,BASIC RES LAB,KANAGAWA 248,JAPAN
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
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Berkessel, A
;
Koch, B
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Koch, B
;
论文数:
引用数:
h-index:
机构:
Toniolo, C
;
Rainaldi, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Rainaldi, M
;
Broxterman, QB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
Broxterman, QB
;
Kaptein, B
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
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
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cologne, Dept Chem, D-50939 Cologne, Germany
Univ Cologne, Dept Chem, D-50939 Cologne, Germany
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
论文数:
0
引用数:
0
h-index:
0
机构:
Ruhr Univ Bochum, Lehrstuhl Organ Chem 2, D-44780 Bochum, Germany
Ruhr Univ Bochum, Lehrstuhl Organ Chem 2, D-44780 Bochum, Germany
Bettinger, HF
.
CHEMPHYSCHEM,
2005,
6
(06)
:1169
-1174
[9]
Asymmetric total synthesis of ent-(-)-roseophilin:: Assignment of absolute configuration
[J].
Boger, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Boger, DL
;
Hong, JY
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
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
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard Uinversity, Cambridge
COREY, EJ
;
NIWA, H
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard Uinversity, Cambridge
NIWA, H
;
FALCK, JR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard Uinversity, Cambridge
FALCK, JR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1979,
101
(06)
:1586
-1587
←
1
2
3
4
5
6
→