SYNTHESIS OF 4-PHOSPHONO(DIFLUOROMETHYL)-D, L-PHENYLALANINE AND N-BOC AND N-FMOC DERIVATIVES SUITABLY PROTECTED FOR SOLID-PHASE SYNTHESIS OF NONHYDROLYZABLE PHOSPHOTYROSYL PEPTIDE ANALOGS

被引：90

作者：

BURKE, TR

SMYTH, MS

OTAKA, A

ROLLER, PP

机构：

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(00)60508-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 4-phosphono(difluoromethyl)-D,L-phenylalanine as well as its diethyl phosphonate analogues bearing either Boc or Fmoc-amino protection are reported. The latter two derivatives were utilized for the solid-phase synthesis of SH2-related peptides containing nonhydrolyzable phosphotyrosyl mimetics.

引用

收藏

页码：4125 / 4128

页数：4

相关论文

共 7 条

[1] PREPARATION OF FLUORO-4-(PHOSPHONOMETHYL)-D,L-PHENYLALANINE AND HYDROXY-4-(PHOSPHONOMETHYL)-D,L-PHENYLALANINE SUITABLY PROTECTED FOR SOLID-PHASE SYNTHESIS OF PEPTIDES CONTAINING HYDROLYTICALLY STABLE ANALOGS OF O-PHOSPHOTYROSINE [J].

BURKE, TR ;

SMYTH, MS ;

NOMIZU, M ;

OTAKA, A ;

ROLLER, PP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1336-1340

[2]

BURKE TR, 1991, SYNTHESIS-STUTTGART, V11, P1019

[3] INHIBITION OF SH2 DOMAIN PHOSPHOPROTEIN ASSOCIATION BY A NONHYDROLYZABLE PHOSPHONOPEPTIDE [J].

DOMCHEK, SM ;

AUGER, KR ;

CHATTERJEE, S ;

BURKE, TR ;

SHOELSON, SE .

BIOCHEMISTRY, 1992, 31 (41) :9865-9870

[4] TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE AS A USEFUL DEPROTECTING REAGENT IN BOTH SOLUTION AND SOLID-PHASE PEPTIDE SYNTHESES [J].

FUJII, N ;

OTAKA, A ;

IKEMURA, O ;

AKAJI, K ;

FUNAKOSHI, S ;

HAYASHI, Y ;

KURODA, Y ;

YAJIMA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (04) :274-275

[5] SOLID-PHASE SYNTHESIS OF PROTECTED PEPTIDE-FRAGMENTS USING A TRIALKOXY-DIPHENYL-METHYLESTER RESIN [J].

RINK, H .

TETRAHEDRON LETTERS, 1987, 28 (33) :3787-3790

[6] SOLID-PHASE SYNTHESIS OF NONHYDROLYZABLE PHOSPHOTYROSYL PEPTIDE ANALOGS WITH N-ALPHA-FMOC-(O,O-DI-TERT-BUTYL)PHOSPHONO-PARA-METHYLPHENYLALANINE [J].

SHOELSON, SE ;

CHATTERJEE, S ;

CHAUDHURI, M ;

BURKE, TR .

TETRAHEDRON LETTERS, 1991, 32 (43) :6061-6064

[7] A GENERAL-METHOD FOR THE PREPARATION OF BENZYLIC ALPHA,ALPHA-DIFLUOROPHOSPHONIC ACIDS - NONHYDROLYZABLE MIMETICS OF PHOSPHOTYROSINE [J].

SMYTH, MS ;

FORD, H ;

BURKE, TR .

TETRAHEDRON LETTERS, 1992, 33 (29) :4137-4140