PROTECTION OF HYDROXY-GROUPS BY SILYLATION - USE IN PEPTIDE-SYNTHESIS AND AS LIPOPHILICITY MODIFIERS FOR PEPTIDES

被引:61
作者
DAVIES, JS
HIGGINBOTHAM, CL
TREMEER, EJ
BROWN, C
TREADGOLD, RC
机构
[1] SMITHKLINE BEECHAM PHARMACEUT,ANALYT SCI,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND
[2] DOW CORNING LTD,BARRY CF6 7YL,S GLAM,WALES
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 22期
关键词
D O I
10.1039/p19920003043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A survey of a series of organosilyl derivatives of serine and tyrosine has shown that they have a satisfactory stability profile for use in peptide synthesis. Only when alkaline conditions were used did side-reactions appear. A range of stability profiles have been determined from a study of organosilyl derivatised dipeptides under different conditions, giving t1/2-values for hydrolysis ranging from 41 to 465 min in acid conditions, yet giving long-term stability at pH-values near to neutrality.
引用
收藏
页码:3043 / 3048
页数:6
相关论文
共 13 条
[1]  
AKAJI K, 1985, CHEM PHARM BULL, V33, P173
[2]   ON THE HYDROLYSIS OF TRIALKYLPHENOXYSILANES .2. [J].
AKERMAN, E .
ACTA CHEMICA SCANDINAVICA, 1957, 11 (02) :373-381
[3]   PEPTIDE-SYNTHESIS .7. SOLID-PHASE SYNTHESIS OF CONOTOXIN-G1 [J].
ATHERTON, E ;
SHEPPARD, RC ;
WARD, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10) :2065-2073
[4]   9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP [J].
CARPINO, LA ;
HAN, GY .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3404-&
[5]   SYNTHESIS, HYDROLYTIC REACTIVITY, AND ANTICANCER EVALUATION OF N-TRIORGANOSILYLATED AND O-TRIORGANOSILYLATED COMPOUNDS AS NEW TYPES OF POTENTIAL PRODRUGS [J].
CHIU, FT ;
CHANG, YH ;
OZKAN, G ;
ZON, G ;
FICHTER, KC ;
PHILLIPS, LR .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1982, 71 (05) :542-551
[6]   THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION [J].
CUNICO, RF ;
BEDELL, L .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4797-4798
[7]  
DAVIES JS, 1987, AMINO ACIDS PEPTIDES, V18, P140
[8]  
DAVIES JS, 1987, J CHEM SOC P1, P107
[9]  
DETAR DF, 1968, COMPUTER PROGRAMS CH, V1, P126
[10]   TOTAL SYNTHESIS OF HUMAN CHOLECYSTOKININ-33 [J].
FUJII, N ;
FUTAKI, S ;
MORIMOTO, H ;
INOUE, K ;
DOI, R ;
TOBE, T ;
YAJIMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :324-325