NOVEL ROUTE TO OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES) - STEREOCONTROLLED SYNTHESIS OF P-CHIRAL OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES)

被引：147

作者：

STEC, WJ

GRAJKOWSKI, A

KOZIOLKIEWICZ, M

UZNANSKI, B

机构：

[1] Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Department of Bioorganic Chemistry, Lodz 90-363

来源：

NUCLEIC ACIDS RESEARCH | 1991年 / 19卷 / 21期

关键词：

D O I：

10.1093/nar/19.21.5883

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：

The synthesis and separation of diastereoisomerically pure 5'-O-DMT-nucleoside 3'-O-(2-thio-1,3,2-oxathiaphospholane) allows their use as synthons in DBU-catalyzed reaction with the 5'-hydroxyl function of solid-support-bound nucleoside moiety. Since this reaction is stereospecific (> 99%), this novel method allows preparation of oligo(nucleoside phosphorothioates) (1) with predetermined chirality at each P-chiral internucleotide phosphorothioate centre.

引用

页码：5883 / 5888

页数：6

共 23 条

[1] OLIGODEOXYNUCLEOSIDE PHOSPHORAMIDATES AND PHOSPHOROTHIOATES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS [J].

AGRAWAL, S ;

GOODCHILD, J ;

CIVEIRA, MP ;

THORNTON, AH ;

SARIN, PS ;

ZAMECNIK, PC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (19) :7079-7083

[2] SOLID-PHASE SYNTHESIS OF DNA UNDER A NON-DEPURINATING CONDITION WITH A BASE LABILE 5'-PROTECTING GROUP (FMOC) USING PHOSPHITEAMIDITE APPROACH [J].

BALGOBIN, N ;

CHATTOPADHYAYA, J .

NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (1-2) :461-463

[3] REGULATION OF GENE-EXPRESSION WITH DOUBLE-STRANDED PHOSPHOROTHIOATE OLIGONUCLEOTIDES [J].

BIELINSKA, A ;

SHIVDASANI, RA ;

ZHANG, LQ ;

NABEL, GJ .

SCIENCE, 1990, 250 (4983) :997-1000

[4] A NEW BASE-STABLE LINKER FOR SOLID-PHASE OLIGONUCLEOTIDE SYNTHESIS [J].

BROWN, T ;

PRITCHARD, CE ;

TURNER, G ;

SALISBURY, SA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :891-893

[5] REVERSIBLE OXIDATION OF PHOSPHYLTHIONATES AND PHOSPHYLSELENONATES WITH TRIFLUOROACETIC-ANHYDRIDE [J].

BRUZIK, KS ;

STEC, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6131-6135

[6] STEREOCHEMICAL COURSE OF THE REACTION CATALYZED BY 5'-NUCLEOTIDE PHOSPHODIESTERASE FROM SNAKE-VENOM [J].

BRYANT, FR ;

BENKOVIC, SJ .

BIOCHEMISTRY, 1979, 18 (13) :2825-2828

[7] ABSOLUTE-CONFIGURATION OF DIASTEREOMERS OF ADENOSINE 5'-O-(1-THIOTRIPHOSPHATE) - CONSEQUENCES FOR STEREOCHEMISTRY OF POLYMERIZATION BY DNA-DEPENDENT RNA-POLYMERASE FROM ESCHERICHIA-COLI [J].

BURGERS, PMJ ;

ECKSTEIN, F .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1978, 75 (10) :4798-4800

[8] AN APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF SP-DINUCLEOSIDE PHOSPHOROTHIOATES USING PHOSPHOTRIESTER CHEMISTRY [J].

COSSTICK, R ;

WILLIAMS, DM .

NUCLEIC ACIDS RESEARCH, 1987, 15 (23) :9921-9932

[9] PHOSPHOROTHIOATE ANALOGS OF NUCLEOTIDES [J].

ECKSTEIN, F .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (06) :204-210

[10] ACYLPHOSPHONATES .7. A NEW METHOD FOR STEREOSPECIFIC AND STEREOSELECTIVE GENERATION OF DIDEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES VIA THE ACYLPHOSPHONATE INTERMEDIATES [J].

FUJII, M ;

OZAKI, K ;

SEKINE, M ;

HATA, T .

TETRAHEDRON, 1987, 43 (15) :3395-3407

← 1 2 3 →