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

被引:104
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
相关论文
共 22 条
[1]   4',6'-METHANO CARBOCYCLIC THYMIDINE - A CONFORMATIONALLY CONSTRAINED BUILDING-BLOCK FOR OLIGONUCLEOTIDES [J].
ALTMANN, KH ;
KESSELRING, R ;
FRANCOTTE, E ;
RIHS, G .
TETRAHEDRON LETTERS, 1994, 35 (15) :2331-2334
[2]   A MOLECULAR MECHANICS STUDY OF CYCLOPROPANES WITHIN THE MM2 AND MM3 FORCE-FIELDS [J].
APED, P ;
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :1-16
[3]   MODELING, SYNTHESIS, AND HYBRIDIZATION PROPERTIES OF (L)-RIBONUCLEIC ACID [J].
ASHLEY, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :9731-9736
[4]   SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].
BORTHWICK, AD ;
BIGGADIKE, K .
TETRAHEDRON, 1992, 48 (04) :571-623
[5]   HIGH-RESOLUTION NMR-STUDY OF A SYNTHETIC DNA-RNA HYBRID DODECAMER CONTAINING THE CONSENSUS PRIBNOW PROMOTER SEQUENCE - D(CGTTATAATGCG).R(CGCAUUAUAACG) [J].
CHOU, SH ;
FLYNN, P ;
REID, B .
BIOCHEMISTRY, 1989, 28 (06) :2435-2443
[6]  
COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585
[7]   STRUCTURE OF A DNA-RNA HYBRID DUPLEX - WHY RNASE-H DOES NOT CLEAVE PURE RNA [J].
FEDOROFF, OY ;
SALAZAR, M ;
REID, BR .
JOURNAL OF MOLECULAR BIOLOGY, 1993, 233 (03) :509-523
[8]  
GAIS HJ, 1986, LIEBIGS ANN CHEM, P687
[9]  
GAIS HJ, 1986, LIEBIGS ANN CHEM, P1179
[10]  
Gait M. J, 1984, OLIGONUCLEOTIDE SYNT