1',6'-METHANO CARBOCYCLIC THYMIDINE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND EFFECT ON NUCLEIC-ACID DUPLEX STABILITY

被引:103
作者
ALTMANN, KH [1 ]
IMWINKELRIED, R [1 ]
KESSELRING, R [1 ]
RIHS, G [1 ]
机构
[1] DEPT PHYS,CH-4002 BASEL,SWITZERLAND
关键词
D O I
10.1016/S0040-4039(00)78359-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound 1 has been synthesized via bicyclic lactone 3 and amine 9 as the key intermediates. X-ray crystallography reveals the bicyclic skeleton of 1 to adopt a boat-like (3'exo) conformation. Oligodeoxyribonucleotides incorporating up to 10 building blocks 1 in place of natural thymidine are still capable of binding to complementary DNA or RNA, albeit with lower affinity than the unmodified parent compounds.
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页码:7625 / 7628
页数:4
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