New approach to the synthesis of oligodeoxyribonucleotides modified with phosphorothioates of predetermined sense of P-chirality

被引:13
作者
Nawrot, B [1 ]
Rebowska, B [1 ]
Cieslinska, K [1 ]
Stec, WJ [1 ]
机构
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Bioorgan Chem, PL-90363 Lodz, Poland
关键词
P-chiral dinucleoside phosphorothioate; oligonucleotide phosphorothioate; PS-DNA; S-protection; oligonucleotide synthesis;
D O I
10.1016/j.tetlet.2005.07.158
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Appropriately protected, diastereomerically pure dinucleoside phosphorothioates, obtained by the stereocontrolled oxathiaphospholane method, were S-alkylated with 2-nitrobenzyl bromide and then converted into their 3 '-0-phosphoramidites. The corresponding S-protected dinucleotide building blocks were successfully used for the synthesis of oligonucleotides containing P-stereodefined phosphorothioate bonds at preselected positions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6641 / 6644
页数:4
相关论文
共 23 条
[1]   Incorporation of terminal phosphorothioates into oligonucleotides [J].
Alefelder, S ;
Patel, BK ;
Eckstein, F .
NUCLEIC ACIDS RESEARCH, 1998, 26 (21) :4983-4988
[2]  
BURGERS PMJ, 1979, J BIOL CHEM, V254, P7476
[3]   GENE SYNTHESIS MACHINES - DNA CHEMISTRY AND ITS USES [J].
CARUTHERS, MH .
SCIENCE, 1985, 230 (4723) :281-285
[4]   SYNTHESIS AND CHARACTERIZATION OF AN OCTANUCLEOTIDE CONTAINING THE ECORI RECOGNITION SEQUENCE WITH A PHOSPHOROTHIOATE GROUP AT THE CLEAVAGE SITE [J].
CONNOLLY, BA ;
POTTER, BVL ;
ECKSTEIN, F ;
PINGOUD, A ;
GROTJAHN, L .
BIOCHEMISTRY, 1984, 23 (15) :3443-3453
[5]   Using phosphorothioate-substituted RNA to investigate the thermodynamic role of phosphates in a sequence specific RNA-protein complex [J].
Dertinger, D ;
Behlen, LS ;
Uhlenbeck, OC .
BIOCHEMISTRY, 2000, 39 (01) :55-63
[6]  
Guga P, 2002, TOP CURR CHEM, V220, P169
[7]  
GUGA P, 2003, CURRENT PROTOCOLS NU
[8]  
GUGA P, UNPUB
[9]   SYNTHESIS OF VARIOUS BRANCHED TRIRIBONUCLEOSIDE DIPHOSPHATES BY SITE-SPECIFIC MODIFICATION OF A DIPHENYLCARBAMOYL-PROTECTED GUANINE RESIDUE [J].
HUSS, S ;
GOSSELIN, G ;
IMBACH, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :499-506
[10]   Isolation of oligodeoxynucleoside phosphorothioate diastereomers by the combination of DEAE ion-exchange and reversed-phase chromatography [J].
Kanehara, K ;
Mizuguchi, M ;
Makino, K .
NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (1-3) :399-406