SYNTHESIS OF DOUBLY CROSS-LINKED CYCLIC HEXAPEPTIDES

被引:2
作者
BAILEY, PD [1 ]
CARTER, SR [1 ]
CLARKE, DGW [1 ]
CROFTS, GA [1 ]
TYSZKA, JHM [1 ]
SMITH, PW [1 ]
WARD, P [1 ]
机构
[1] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)79854-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic hexapeptides in which the adjacent N(epsilon)-nitrogens of cyclo-(Lys-Lys-Gly)2 are cross-linked by p-xylyl or (CH2)6 units have been prepared. The key steps in the syntheses of these novel types of peptide were the use of tosyl (or, less efficiently, trifluoroacetyl) as N(epsilon)-protection that allowed intramolecular cross-linking of the tripeptides Boc-Lys(R)-Lys(R)-Gly-OMe (R = Ts or CF3CO) using alpha,omega-dibromo-alkanes/ Cs2CO3, and the efficient cyclo-dimerisation of the pentafluoro-phenyl esters of the resultant cross-linked tripeptides.
引用
收藏
页码:3211 / 3214
页数:4
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