A-FMOC-4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE - A NEW O-PHOSPHOTYROSINE ISOSTERIC BUILDING-BLOCK SUITABLE FOR DIRECT INCORPORATION INTO PEPTIDES

Authors
GORDEEV MF PATEL DV BARKER PL GORDON EM
Citation
Mf. Gordeev et al., A-FMOC-4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE - A NEW O-PHOSPHOTYROSINE ISOSTERIC BUILDING-BLOCK SUITABLE FOR DIRECT INCORPORATION INTO PEPTIDES, Tetrahedron letters, 35(41), 1994, pp. 7585-7588
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
41
Year of publication
1994
Pages
7585 - 7588
Database
ISI
SICI code
0040-4039(1994)35:41<7585:A-ANO>2.0.ZU;2-3
Abstract
An efficient preparation of ha-Fmoc-4-phospono(difluoromethyl)-L-pheny lalanine 5 is described. The synthesis of this phosphotyrosine isoster e involves deprotection of the penultimate diethylphosphonate intermed iate 4 with BSTFA/TMS1 as the key step. Building block 5 can be utiliz ed directly for incorporation into peptides without protection of the side chain phosphonic acid group, as illustrated by the efficient prep aration of model difluorophosphonopeptides Ac-F(2)Pmy-Ile-Asn-Gln-NH2 and Ac-Glu-F(2)Pmp-Ile-Asn-Gln-NH2.