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

被引：36

作者：

GORDEEV, MF

PATEL, DV

BARKER, PL

GORDON, EM

机构：

[1] Affymax Research Institute, Santa Clara, CA 95051

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)78349-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient preparation of N-alpha-Fmoc-4-phospono(difluoromethyl)-L-phenylalanine 5 is described. The synthesis of this phosphotyrosine isostere involves deprotection of the penultimate diethylphosphonate intermediate 4 with BSTFA/TMS1 as the key step. Building block 5 can be utilized directly for incorporation into peptides without protection of the side chain phosphonic acid group, as illustrated by the efficient preparation of model difluorophosphonopeptides Ac-F(2)Pmy-Ile-Asn-Gln-NH2 and Ac-Glu-F(2)Pmp-Ile-Asn-Gln-NH2.

引用

页码：7585 / 7588

页数：4

共 23 条

[21] BINDING OF A HIGH-AFFINITY PHOSPHOTYROSYL PEPTIDE TO THE SRC SH2 DOMAIN - CRYSTAL-STRUCTURES OF THE COMPLEXED AND PEPTIDE-FREE FORMS [J].