A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon.

Authors
Georgiadis, D Matziari, M Vassiliou, S Dive, V Yiotakis, A
Citation
D. Georgiadis et al., A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon., TETRAHEDRON, 55(51), 1999, pp. 14635-14648
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
51
Year of publication
1999
Pages
14635 - 14648
Database
ISI
SICI code
0040-4020(199912)55:51<14635:ACMTSP>2.0.ZU;2-0
Abstract
Many attempts to synthesize Asp Psi(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achiev ed starting from a protected Phe Psi(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system. (C) 1999 Else vier Science Ltd. All rights reserved.