4-benchrotrenyl pyrylium salts as protein organometallic labelling reagents

被引:24
作者
Caro, B
Le Guen-Robin, F
Salmain, M
Jaouen, G
机构
[1] Ecole Natl Super Chim Paris, Lab Chim Organomet, CNRS, UMR 7576, F-75231 Paris 05, France
[2] IUT, Lab Chim Organomet & Biol, CNRS, UMR 6509, F-22302 Lannion, France
关键词
D O I
10.1016/S0040-4020(99)00947-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrylium ions are useful reagents to selectively modify the amino group of protein lysine residues. This property was exploited here to label proteins with chromium tricarbonyl complexes in the form of 4-benchrotrenyl pyridinium ions. Kinetic studies of the reaction of a series of benchrotrenyl pyrylium salts with water and n-butylamine were performed and revealed that the overall reactivity of these compounds was highly dependent on their substitution pattern. These compounds could find application in protein X-ray crystallography. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:257 / 263
页数:7
相关论文
共 22 条
[1]  
BALABHAN AT, 1982, ADV HETEROCYCLIC C S, V2, P114
[2]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[3]  
BRANDEN C, 1991, INTRO PROTEIN STRUCT, P269
[4]   DIACETYLATION OF ETHYLENE COMPOUNDS OF BENZENE CHROMIUMTRICARBONYL - PREPARATION OF GAMMA-BENCHROTRENIC PYRYLIUM-SALTS - X-RAY STRUCTURAL-ANALYSIS AND UNUSUAL ELECTRON BEHAVIOR OF THE CR(CO)3 GROUP [J].
CARO, B ;
SENECHALTOCQUER, MC ;
SENECHAL, D ;
MARREC, P ;
SAILLARD, JY ;
TRIKI, S ;
KAHLAL, S .
TETRAHEDRON LETTERS, 1993, 34 (45) :7259-7262
[5]  
CARO B, 1997, J ORGANOMET CHEM, P543
[6]   C-13-NUCLEAR MAGNETIC-RESONANCE STUDY OF GLYCOPHORIN-AM AND GLYCOPHORIN-AN MODIFIED WITH VARIOUS PYRYLIUM SALTS [J].
DILL, K ;
HU, SH ;
SUTHARCHANADEVI, M ;
KATRITZKY, AR .
JOURNAL OF PROTEIN CHEMISTRY, 1988, 7 (04) :341-348
[7]   INHIBITION OF THE NA+ GLUCOSE COTRANSPORTER FUNCTIONAL LYSYL RESIDUES BY 4-(4-METHOXY-3-SULFOPHENYL)-2,6-BIS(4-SULFOPHENYL)PYRYLIUM [J].
FERNANDEZ, A ;
KATRITZKY, AR ;
SUTHARCHANADEVI, M ;
STEVENS, BR .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 163 (03) :1356-1363
[8]   ELECTRONIC EFFECTS IN GROUP VIB ARENE-METAL CARBONYL COMPLEXES AND RELATED SPECIES [J].
HOLMES, JD ;
JONES, DAK ;
PETTIT, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1965, 4 (04) :324-&
[9]   PYRYLIUM-MEDIATED TRANSFORMATIONS OF NATURAL-PRODUCTS .1. SYNTHESIS AND HYDROLYSIS OF 4-(4-METHOXY-3-SULPHOPHENYL)-2,6-BIS-(4-SULPHOPHENYL)PYRYLIUM PERCHLORATE - A NEW WATER-SOLUBLE PYRYLIUM CATION [J].
KATRITZKY, AR ;
DEROSA, M ;
GRZESKOWIAK, NE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (05) :841-847
[10]   PYRYLIUM-MEDIATED TRANSFORMATIONS OF NATURAL-PRODUCTS .4. REACTIONS OF WATER-SOLUBLE PYRYLIUM-SALTS WITH WATER AND WITH AMINES [J].
KATRITZKY, AR ;
LEAHY, DE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (05) :867-873