A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids

被引:113
作者
Brun, MP
Bischoff, L
Garbay, C
机构
[1] Univ Paris 05, UFR Biomed, CNRS, FRE 2718,INSERM,U648,Lab Pharmacochim Mol & Cellu, F-75270 Paris 06, France
[2] INSA, UPRESA 6014, IRCOF, F-76131 Mont St Aignan, France
关键词
amino acids; coumarin; cyclization; fluorescent probes; solid-phase synthesis;
D O I
10.1002/anie.200454116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
No bulkier than a tryptophan or a tyrosine residue are the fluorescent coumaryl amino acids described. These building blocks can be synthesized rapidly with high enantiomeric purity and introduced readily into a peptidic sequence. Their fluorescence properties allow, for example, the investigation of the cellular localization of labeled peptides through confocal fluorescence microscopy (see picture).
引用
收藏
页码:3432 / 3436
页数:5
相关论文
共 37 条
[1]   The efficient, enantioselective synthesis of quinoxaline, pyrazine and 1,2,4-triazine substituted α-amino acids from vicinal tricarbonyls [J].
Adlington, RM ;
Baldwin, JE ;
Catterick, D ;
Pritchard, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07) :668-679
[2]  
[Anonymous], 1992, ALDRICHIM ACTA
[3]   L-(6,7-dimethoxy-4-coumaryl) alanine: an intrinsic probe for the labelling of peptides [J].
Bennett, FA ;
Barlow, DJ ;
Dodoo, ANO ;
Hider, RC ;
Lansley, AB ;
Lawrence, MJ ;
Marriott, C ;
Bansal, SS .
TETRAHEDRON LETTERS, 1997, 38 (42) :7449-7452
[4]  
Bose DS, 2002, TETRAHEDRON LETT, V43, P9195
[5]   SYNTHESIS AND CHARACTERIZATION OF SELECTIVE FLUORESCENT LIGANDS FOR THE NEUROKININ NK2 RECEPTOR [J].
BRADSHAW, CG ;
CESZKOWSKI, K ;
TURCATTI, G ;
BERESFORD, IJM ;
CHOLLET, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (13) :1991-1995
[6]  
Brooks D. W., 1979, ANGEW CHEM, V91, P76
[7]   C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].
BROOKS, DW ;
LU, LDL ;
MASAMUNE, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74
[8]  
Brufola G, 1996, HETEROCYCLES, V43, P1257
[9]   An alternative route to the proline derivative (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid from protected glutamic acid [J].
Brun, MP ;
Martin, AS ;
Garbay, C ;
Bischoff, L .
TETRAHEDRON LETTERS, 2003, 44 (37) :7011-7013
[10]   Zinc mediated transesterification of β-ketoesters and coumarin synthesis [J].
Chavan, SP ;
Shivasankar, K ;
Sivappa, R ;
Kale, R .
TETRAHEDRON LETTERS, 2002, 43 (47) :8583-8586