DEPROTECTION AND CLEAVAGE METHODS FOR PROTECTED PEPTIDE RESINS CONTAINING 4-[(DIETHYLPHOSPHONO)DIFLUOROMETHYL]-D,L-PHENYLALANINE RESIDUES

被引:32
作者
OTAKA, A
BURKE, TR
SMYTH, MS
NOMIZU, M
ROLLER, PP
机构
关键词
D O I
10.1016/S0040-4039(00)61591-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ethyl groups on 4-[(diethylphosphono)difluoromethyl]-D,L-phenylalanine are efficiently removed using S(N)2-type acidic reagents. These methods were utilized for the solid-phase synthesis of SH2-binding peptides containing nonhydrolyzable phosphotyrosyl mimetics.
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页码:7039 / 7042
页数:4
相关论文
共 16 条
[1]   PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].
ALBERICIO, F ;
KNEIBCORDONIER, N ;
BIANCALANA, S ;
GERA, L ;
MASADA, RI ;
HUDSON, D ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743
[2]   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 [J].
BURKE, TR ;
SMYTH, MS ;
OTAKA, A ;
ROLLER, PP .
TETRAHEDRON LETTERS, 1993, 34 (26) :4125-4128
[3]   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
[4]  
BURKE TR, 1991, SYNTHESIS-STUTTGART, V11, P1019
[5]   RECEPTOR TYROSINE KINASE SUBSTRATES - SRC HOMOLOGY DOMAINS AND SIGNAL TRANSDUCTION [J].
CARPENTER, G .
FASEB JOURNAL, 1992, 6 (14) :3283-3289
[6]   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
[7]   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
[8]  
FUJII N, 1987, CHEM PHARM BULL, V35, P3880
[9]  
GARBAYJAUREGUIBERRY C, 1992, INT J PEPT PROT RES, V39, P523
[10]   FMOC-POLYAMIDE SOLID-PHASE SYNTHESIS OF AN O-PHOSPHOTYROSINE-CONTAINING TRIDECAPEPTIDE [J].
KITAS, EA ;
PERICH, JW ;
WADE, JD ;
JOHNS, RB ;
TREGEAR, GW .
TETRAHEDRON LETTERS, 1989, 30 (45) :6229-6232