Synthesis and conformation of 3'-O,4'-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2',5'-linked oligonucleotide modification

被引:63
作者
Obika, S [1 ]
Morio, K [1 ]
Nanbu, D [1 ]
Imanishi, T [1 ]
机构
[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN
关键词
D O I
10.1039/a704376g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel bicyclic nucleoside analogues 3'-O,4'-C-methylene-ribonucleosides 1 are conveniently prepared starting from uridine; the sugar puckering of 1 is found to be nearly in the S-conformation by means of PM3 calculations and H-1 NMR studies.
引用
收藏
页码:1643 / 1644
页数:2
相关论文
共 26 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]   CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION [J].
ALTONA, C ;
SUNDARALINGAM, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) :8205-+
[3]   CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - IMPROVED METHOD FOR INTERPRETATION OF PROTON MAGNETIC-RESONANCE COUPLING-CONSTANTS [J].
ALTONA, C ;
SUNDARALINGAM, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2333-2344
[4]   DIMENSIONS AND SHAPES OF FURANOSE RINGS IN NUCLEIC-ACIDS [J].
ARNOTT, S ;
HUKINS, DWL .
BIOCHEMICAL JOURNAL, 1972, 130 (02) :453-+
[5]   NUCLEOSIDE 4',5'-ENOL ACETATES - SYNTHESIS AND CHEMISTRY OF A UNIQUE URIDINE O2,4'-ANHYDRONUCLEOSIDE [J].
COOK, SL ;
SECRIST, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1554-1564
[6]   OLIGODEOXYNUCLEOTIDES THAT CONTAIN 2',5'' LINKAGES - SYNTHESIS AND HYBRIDIZATION PROPERTIES [J].
DOUGHERTY, JP ;
RIZZO, CJ ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6254-6255
[7]   OLIGORIBONUCLEOTIDES CONTAINING 2',5'-PHOSPHODIESTER LINKAGES EXHIBIT BINDING SELECTIVITY FOR 3',5'-RNA OVER 3',5'-SSDNA [J].
GIANNARIS, PA ;
DAMHA, MJ .
NUCLEIC ACIDS RESEARCH, 1993, 21 (20) :4742-4749
[8]   SELF-ASSOCIATION OF 2',5'-LINKED DEOXYNUCLEOTIDES - META-DNA [J].
HASHIMOTO, H ;
SWITZER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6255-6256
[9]   Nucleotides .47. Synthesis of 3'-deoxyadenylyl-(2'-5')-3'-deoxyadenylyl-(2'-5')-3'-O-(2-hydroxyethyl)adenosine and 3'-deoxyadenylyl-(2'-5')-3'-deoxyadenylyl-(2'-5'-3'-O-{2-[(cholest-5-en-3 beta-yloxy)carbonyloxy]ethyl}adenosine: A new type of (2'-5')adenylate trimer conjugate [J].
Horndler, C ;
Pfleiderer, W .
HELVETICA CHIMICA ACTA, 1996, 79 (03) :718-726
[10]   4'-SUBSTITUTED NUCLEOSIDES .5. HYDROXYMETHYLATION OF NUCLEOSIDE 5'-ALDEHYDES [J].
JONES, GH ;
TANIGUCHI, M ;
TEGG, D ;
MOFFATT, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08) :1309-1317