SYNTHESIS AND CHARACTERIZATION OF NUCLEOSIDE PEPTIDES - TOWARD CHEMICAL RIBONUCLEASES .1.

被引:55
作者
BASHKIN, JK
GARD, JK
MODAK, AS
机构
[1] Monsanto Company, St. Louis
关键词
D O I
10.1021/jo00304a026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Site-selective cleavage of nucleic acids by chemical analogues of nuclease enzymes is an area of major interest. Since imidazole is known to catalyze the hydrolysis of RNA, we postulated that oligonucleotides with pendant imidazole groups could be used to hydrolyze RNA in a sequence specific manner, utilizing complementarity, the natural nucleic acid recognition mechanism. We report here the synthesis and complete characterization of a series of uridine–imidazole conjugates which are based on C-5 substituted deoxyuridine. The nucleoside is joined with a variable-length linker arm to histidine or related imidazole-containing moieties, and protecting groups were employed to allow the subsequent conversion of the nucleoside–peptides into phosphoramidites suitable for oligonucleotide synthesis. Extensive multidimensional NMR characterization of the novel nucleoside–peptides is reported. © 1990, American Chemical Society. All rights reserved.
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页码:5125 / 5132
页数:8
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