Synthesis of dimer phosphoramidite synthons for oligodeoxyribonucleotide phosphorothioates using diethyldithiocarbonate disulfide as an efficient sulfurizing reagent

被引：16

作者：

Eleuteri, A ^{[1
]}

Cheruvallath, ZS ^{[1
]}

Capaldi, DC ^{[1
]}

Cole, DL ^{[1
]}

Ravikumar, VT ^{[1
]}

机构：

[1] ISIS Pharmaceut, Carlsbad, CA 92008 USA

来源：

NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 08期

关键词：

D O I：

10.1080/07328319908044844

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient solution phase synthesis of deoxyribonucleoside phosphorothioate dimers utilizing phosphoramidite approach is described. Diethyldithiocarbonate disulfide (DDD) was found to be an efficient sulfurizing reagent in the conversion of phosphite triesters to phosphorothioate triesters.

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收藏

页码：1803 / 1807

页数：5

相关论文

共 22 条

[1] ABSORPTION, TISSUE DISTRIBUTION AND IN-VIVO STABILITY IN RATS OF A HYBRID ANTISENSE OLIGONUCLEOTIDE FOLLOWING ORAL-ADMINISTRATION [J].

AGRAWAL, S ;

ZHANG, XS ;

LU, ZH ;

ZHAO, H ;

TAMBURIN, JM ;

YAN, YM ;

CAI, HY ;

DIASIO, RB ;

HABUS, I ;

JIANG, ZW ;

IYER, RP ;

YU, D ;

ZHANG, RW .

BIOCHEMICAL PHARMACOLOGY, 1995, 50 (04) :571-576

[2] A GENERAL STRATEGY FOR ELABORATION OF THE DITHIOCARBONYL FUNCTIONALITY, -(C=O)SS- - APPLICATION TO THE SYNTHESIS OF BIS(CHLOROCARBONYL)DISULFANE AND RELATED DERIVATIVES OF THIOCARBONIC ACIDS [J].

BARANY, G ;

SCHROLL, AL ;

MOTT, AW ;

HALSRUD, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4750-4761

[3] ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].

BEAUCAGE, SL ;

IYER, RP .

TETRAHEDRON, 1992, 48 (12) :2223-2311

[4] THE SYNTHESIS OF MODIFIED OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH AND THEIR APPLICATIONS [J].

BEAUCAGE, SL ;

IYER, RP .

TETRAHEDRON, 1993, 49 (28) :6123-6194

[5] THE CHEMISTRY OF XANTHIC ACID DERIVATIVES .2. THE THERMAL DECOMPOSITION OF DISULPHURDICARBOTHIONIC ESTERS [J].

BULMER, G ;

MANN, FG .

JOURNAL OF THE CHEMICAL SOCIETY, 1945, (SEP-) :674-677

[6]

Crooke S. T., 1995, THERAPEUTIC APPL OLI

[7] A PHARMACOKINETIC EVALUATION OF C-14-LABELED AFOVIRSEN SODIUM IN PATIENTS WITH GENITAL WARTS [J].

CROOKE, ST ;

GRILLONE, LR ;

TENDOLKAR, A ;

GARRETT, A ;

FRATKIN, MJ ;

LEEDS, J ;

BARR, WH .

CLINICAL PHARMACOLOGY & THERAPEUTICS, 1994, 56 (06) :641-646

[8]

CROOKE ST, 1994, PROGR OLIGONUCLEOTID

[9]

CROOKE ST, 1995, BURGERS MED CHEM DRU, V1, P863

[10] INVESTIGATION OF THE N-1 IMPURITY IN PHOSPHOROTHIOATE OLIGODEOXYNUCLEOTIDES SYNTHESIZED BY THE SOLID-PHASE BETA-CYANOETHYL PHOSPHORAMIDITE METHOD USING STEPWISE SULFURIZATION [J].

FEARON, KL ;

STULTS, JT ;

BERGOT, BJ ;

CHRISTENSEN, LM ;

RAIBLE, AM .

NUCLEIC ACIDS RESEARCH, 1995, 23 (14) :2754-2761