2′-deoxy-2′(S)-ethinyl oligonucleotides:: A modification which selectively stabilizes oligoadenylate pairing to DNA complements

被引:18
作者
Buff, R [1 ]
Hunziker, J [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
D O I
10.1016/S0960-894X(98)00060-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Oligonucleotides consisting of 2'-deoxy-2'(S)-ethinyl-thymidine, -uridine, and -adenosine have been prepared. Whereas the modified pyrimidine oligonucleotides uniformly lead to weaker pairing affinity with DNA and RNA complements, the corresponding adenine oligonucleotides show enhanced thermal stability in duplexes with complementary DNA and decreased stability with RNA. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:521 / 524
页数:4
相关论文
共 16 条
[1]   1',6'-METHANO CARBOCYCLIC THYMIDINE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND EFFECT ON NUCLEIC-ACID DUPLEX STABILITY [J].
ALTMANN, KH ;
IMWINKELRIED, R ;
KESSELRING, R ;
RIHS, G .
TETRAHEDRON LETTERS, 1994, 35 (41) :7625-7628
[2]  
BUFF R, UNPUB ACTA CRYST C
[3]  
CONOLLY BA, 1991, OLIGONUCLEOTIDES ANA, P155
[4]   The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes [J].
Freier, SM ;
Altmann, KH .
NUCLEIC ACIDS RESEARCH, 1997, 25 (22) :4429-4443
[5]   1',5'-anhydrohexitol oligonucleotides: Hybridisation and strand displacement with oligoribonucleotides, interaction with RNase H and HIV reverse transcriptase [J].
Hendrix, C ;
Rosemeyer, H ;
DeBouvere, B ;
VanAerschot, A ;
Seela, F ;
Herdewijn, P .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (09) :1513-1520
[6]  
HUNZIKER J, 1995, MODERN SYNTHETIC MET, V7, P331
[7]   NUCLEOSIDES AND NUCLEOTIDES .134. SYNTHESIS OF 2'-C-ALKYNYL-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLPYRIMIDINES VIA RADICAL DEOXYGENATION OF TERT-PROPARGYL ALCOHOLS IN THE SUGAR MOIETY [J].
IINO, T ;
YOSHIMURA, Y ;
MATSUDA, A .
TETRAHEDRON, 1994, 50 (35) :10397-10406
[8]   Preorganization of DNA: Design principles for improving nucleic acid recognition by synthetic oligonucleotides [J].
Kool, ET .
CHEMICAL REVIEWS, 1997, 97 (05) :1473-1487
[9]  
MCCARTHY JR, Patent No. 0365849
[10]  
NIELSEN P, 1997, J CHEM SOC CHEM COMM, P825