Convergent synthesis of potent peptide inhibitors of the Grb2-SH2 domain by palladium catalyzed coupling of a terminal alkyne

Authors
Schoepfer, J Gay, B End, N Muller, E Scheffel, G Caravatti, G Furet, P
Citation
J. Schoepfer et al., Convergent synthesis of potent peptide inhibitors of the Grb2-SH2 domain by palladium catalyzed coupling of a terminal alkyne, BIOORG MED, 11(9), 2001, pp. 1201-1203
Citations number
15
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
9
Year of publication
2001
Pages
1201 - 1203
Database
ISI
SICI code
0960-894X(20010507)11:9<1201:CSOPPI>2.0.ZU;2-C
Abstract
A new strategy was developed to prepare in a very efficient and convergent manner C-terminal modified tripeptides with high affinities for the Grb2-SH 2 domain. Using Pd(PPh3)(2)Cl-2 as catalyst, selected naphthyl iodides and triflates were coupled to Ac-Pmp(t-Bu)(2)-Ac(6)c-Asn-NH(prop-2-ynyl). The r esulting alkyne derivatives were hydrogenated and deprotected to afford pot ent Grb2-SH2 inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved .