STEREOSELECTIVE MODIFICATION OF A CYCLOPENTAPEPTIDE VIA AN ALPHA-(ETHYLTHIO)GLYCINE RESIDUE

Authors
PAULITZ C STEGLICH W
Citation
C. Paulitz et W. Steglich, STEREOSELECTIVE MODIFICATION OF A CYCLOPENTAPEPTIDE VIA AN ALPHA-(ETHYLTHIO)GLYCINE RESIDUE, Journal of organic chemistry, 62(24), 1997, pp. 8474-8478
Citations number
44
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
24
Year of publication
1997
Pages
8474 - 8478
Database
ISI
SICI code
0022-3263(1997)62:24<8474:SMOACV>2.0.ZU;2-W
Abstract
The solid-phase synthesis of cyclo[Val-D-Gly(SEt)-Pro-Phe-D-Ala] (5) o n Kaiser's oxime resin is described. Conversion of 5 to the reactive a lpha-chloroglycine derivative 9 allowed the stereoselective addition o f thiols, alcohols, amines and other nucleophiles with formation of th e modified cyclopeptides 11a-n.