Synthesis of silicon analogues of acyclonucleotides incorporable in oligonucleotide solid-phase synthesis

被引:29
作者
Thibon, J [1 ]
Latxague, L [1 ]
Deleris, G [1 ]
机构
[1] UNIV BORDEAUX 2,CHIM BIOORGAN LAB,F-33076 BORDEAUX,FRANCE
关键词
D O I
10.1021/jo962165p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the four silicon analogues of acyclonucleosides was described. In every case, the silicon atom was introduced onto an allyl group on the natural nucleobase following a hydrosilylation reaction. Diols obtained were protected as 4,4'-dimethoxytrityl ethers and subsequently activated as 2-cyanoethyl N,N-diisopropylchlorophosphoramidite in order to be suitable for oligonucleotide solid phase synthesis.
引用
收藏
页码:4635 / 4642
页数:8
相关论文
共 21 条
[1]  
COHEN JS, 1987, OLIGODEOXYNUCLEOTIDE
[2]   SYNTHESIS OF THE POLYCATION THYMIDYL DNG, ITS FIDELITY IN BINDING POLYANIONIC DNA/RNA, AND THE STABILITY AND NATURE OF THE HYBRID COMPLEXES [J].
DEMPCY, RO ;
BROWNE, KA ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :6140-6141
[3]   BOND ORDER AND CHARGE LOCALIZATION IN NUCLEOSIDE PHOSPHOROTHIOATES [J].
FREY, PA ;
SAMMONS, RD .
SCIENCE, 1985, 228 (4699) :541-545
[4]   REGIOCHEMISTRY AND STEREOCHEMISTRY IN PD(0)-CATALYZED ALLYLIC ALKYLATION OF NUCLEOSIDE BASES [J].
GUNDERSEN, LL ;
BENNECHE, T ;
RISE, F ;
GOGOLL, A ;
UNDHEIM, K .
ACTA CHEMICA SCANDINAVICA, 1992, 46 (08) :761-771
[5]   SPECIFIC REGULATION OF GENE-EXPRESSION BY ANTISENSE, SENSE AND ANTIGENE NUCLEIC-ACIDS [J].
HELENE, C ;
TOULME, JJ .
BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1049 (02) :99-125
[6]   SELECTIVE ALKYLATION AND ARALKYLATION OF CYTOSINE AT THE 1-POSITION [J].
HELFER, DL ;
HOSMANE, RS ;
LEONARD, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4803-4804
[7]   PHOSPHORUS OXYGEN BOND ORDER IN ADENOSINE 5'-O-PHOSPHOROTHIOATE DIANION [J].
IYENGAR, R ;
ECKSTEIN, F ;
FREY, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8309-8310
[8]  
KONDO K, 1972, MAKROMOLEKUL CHEM, V160, P341
[9]   SYNTHESIS OF SILICON PRECURSORS OF MODIFIED OLIGONUCLEOTIDES [J].
LATXAGUE, L ;
THIBON, J ;
GUILLOT, C ;
MOREAU, S ;
DELERIS, G .
TETRAHEDRON LETTERS, 1994, 35 (32) :5869-5872
[10]   ANTIVIRAL AND RING-OPEN NUCLEOSIDE ANALOGS .5. SYNTHESIS OF A PURINE ACYCLONUCLEOSIDE SERIES HAVING PRONOUNCED ANTIVIRAL ACTIVITY - THE GLYCEROPURINES [J].
OGILVIE, KK ;
NGUYENBA, N ;
GILLEN, MF ;
RADATUS, BK ;
CHERIYAN, UO ;
HANNA, HR ;
SMITH, KO ;
GALLOWAY, KS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :241-252