Rapid analysis of solvent effects on enamine formation by fluorescence: how might enzymes facilitate enamine chemistry with primary amines?

被引：75

作者：

Tanaka, F

Thayumanavan, R

Mase, N

Barbas, CF

机构：

[1] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 02期

基金：

美国国家卫生研究院;

关键词：

enamine; primary amines; solvent effects; fluorescent screening;

D O I：

10.1016/j.tetlet.2003.10.157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to determine factors that facilitate the use of primary amines in biological chemistry, solvent effects on enamine formation with glycine were studied. Solvent effects were rapidly analyzed by monitoring the increase in fluorescence resulting from the reaction between a fluorogenic maleimide and in situ-generated enamine of acetone. These studies suggest that in addition to a simple hydrophobic microenvironment, a microenvironment that also affords for hydrogen bond formation facilitates enamine-based reactions involving primary amines. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：325 / 328

页数：4

共 37 条

[1] Covalent intermediate trapped in 2-keto-3-deoxy-6-phosphogluconate (KDPG) aldolase structure at 1.95-Å resolution
Allard, J
Grochulski, P
Sygusch, J
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (07) : 3679 - 3684
[2] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity
Bahmanyar, S
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) : 11273 - 11283
[3] Immune versus natural selection: Antibody aldolases with enzymic rates but broader scope
Barbas, CF
Heine, A
Zhong, GF
Hoffmann, T
Gramatikova, S
Bjornestedt, R
List, B
Anderson, J
Stura, EA
Wilson, IA
Lerner, RA
[J]. SCIENCE, 1997, 278 (5346) : 2085 - 2092
[4] KINETICS OF PROTON-TRANSFER OF 3,5-HEPTANEDIONE, 2,6-DIMETHYL-3,5-HEPTANEDIONE, AND DIBENZOYLMETHANE WITH AMINES IN 50-PERCENT ME2SO-50-PERCENT WATER - EFFECT OF STERIC CROWDING AND PI-OVERLAP ON INTRINSIC RATE CONSTANTS
BERNASCONI, CF
OHLBERG, DAA
STRONACH, MW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) : 3016 - 3020
[5] Bishop RH, 2002, The mechatronics handbook, P1
[6] Product binding and role of the C-terminal region in class I D-fructose 1,6-bisphosphate aldolase
Blom, N
Sygusch, J
[J]. NATURE STRUCTURAL BIOLOGY, 1997, 4 (01) : 36 - 39
[7] Snapshots of catalysis: The structure of fructose-1,6-(bis)phosphate aldolase covalently bound to the substrate dihydroxyacetone phosphate
Choi, KH
Shi, J
Hopkins, CE
Tolan, DR
Allen, KN
[J]. BIOCHEMISTRY, 2001, 40 (46) : 13868 - 13875
[8] STRUCTURAL AND THERMODYNAMIC CONSEQUENCES OF BURYING A CHARGED RESIDUE WITHIN THE HYDROPHOBIC CORE OF T4 LYSOZYME
DAOPIN, S
ANDERSON, DE
BAASE, WA
DAHLQUIST, FW
MATTHEWS, BW
[J]. BIOCHEMISTRY, 1991, 30 (49) : 11521 - 11529
[9] REVERSIBLE MODIFICATION OF AMINO-GROUPS IN ASPARTATE-AMINOTRANSFERASE
GILBERT, HF
OLEARY, MH
[J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1977, 483 (01) : 79 - 89
[10] MODIFICATION OF ARGININE AND LYSINE IN PROTEINS WITH 2,4-PENTANEDIONE
GILBERT, HF
OLEARY, MH
[J]. BIOCHEMISTRY, 1975, 14 (23) : 5194 - 5199

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