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

被引:60
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.
    AKERMAN, E
    [J]. ACTA CHEMICA SCANDINAVICA, 1957, 11 (02): : 373 - 381
  • [3] PEPTIDE-SYNTHESIS .7. SOLID-PHASE SYNTHESIS OF CONOTOXIN-G1
    ATHERTON, E
    SHEPPARD, RC
    WARD, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10): : 2065 - 2073
  • [4] 9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP
    CARPINO, LA
    HAN, GY
    [J]. 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
    CHIU, FT
    CHANG, YH
    OZKAN, G
    ZON, G
    FICHTER, KC
    PHILLIPS, LR
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1982, 71 (05) : 542 - 551
  • [6] THE TRIISOPROPYLSILYL GROUP AS A HYDROXYL-PROTECTING FUNCTION
    CUNICO, RF
    BEDELL, L
    [J]. 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
    FUJII, N
    FUTAKI, S
    MORIMOTO, H
    INOUE, K
    DOI, R
    TOBE, T
    YAJIMA, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 324 - 325