A METHOD FOR PREPARING OLIGODEOXYNUCLEOTIDES CONTAINING AN APURINIC SITE

被引：22

作者：

GROEBKE, K ^{[1
]}

LEUMANN, C ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,UNIV STR 16,CH-8092 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 03期

关键词：

D O I：

10.1002/hlca.19900730309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In three steps, 2‐deoxy‐D‐ribose has been converted into a phosphoramidite building block bearing a (t‐Bu)Me2Si protecting group at the OH function of the anomeric centre of the furanose ring. This building block was subsequently incorporated into DNA oligomers of various base sequences using the standard phosphoramidite protocol for automated DNA synthesis. The resulting silyl‐oligomers have been purified by HPLC and selectively desilylated to the corresponding free apurinic DNA sequences. The hexamer d (A‐A‐A‐A‐X‐A) (X representing the apurinic site) which was prepared in this way was characterized by 1H‐ and 31P‐NMR spectroscopy. The other sequences as well as their fragments, which formed upon treatment with alkali base, were analyzed by polyacrylamide gel electrophoresis. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：608 / 617

页数：10

共 30 条

[1] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES [J].

BANNWARTH, W ;

TRZECIAK, A .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :175-186

[2] INSITU ACTIVATION OF BIS-DIALKYLAMINOPHOSPHINES - A NEW METHOD FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES ON POLYMER SUPPORTS [J].

BARONE, AD ;

TANG, JY ;

CARUTHERS, MH .

NUCLEIC ACIDS RESEARCH, 1984, 12 (10) :4051-4061

[3] A GENERAL-METHOD FOR DETERMINING THE ANOMERIC CONFIGURATION OF C-FURANOSIDE DERIVATIVES - A H-1 NUCLEAR-MAGNETIC-RESONANCE NUCLEAR OVERHAUSER EFFECT STUDY [J].

BERNSTEIN, MA ;

MORTON, HE ;

GUINDON, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (08) :1155-1163

[4] SYNTHESIS, THERMAL-STABILITY AND REACTIVITY TOWARDS 9-AMINOELLIPTICINE OF DOUBLE-STRANDED OLIGONUCLEOTIDES CONTAINING A TRUE ABASIC SITE [J].

BERTRAND, JR ;

VASSEUR, JJ ;

RAYNER, B ;

IMBACH, JL ;

PAOLETTI, J ;

PAOLETTI, C ;

MALVY, C .

NUCLEIC ACIDS RESEARCH, 1989, 17 (24) :10307-10319

[5] On d-ribose - (Representation of a crystallised anhydroribose). [J].

Bredereck, H ;

Kothnig, M ;

Berger, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1940, 73 :956-962

[6] SOLID-PHASE SYNTHESIS AND HIGH-RESOLUTION NMR-STUDIES OF 2 SYNTHETIC DOUBLE-HELICAL RNA DODECAMERS - R(CGCGAAUUCGCG) AND R(CGCGUAUACGCG) [J].

CHOU, SH ;

FLYNN, P ;

REID, B .

BIOCHEMISTRY, 1989, 28 (06) :2422-2435

[7] AN ABASIC SITE IN DNA - SOLUTION CONFORMATION DETERMINED BY PROTON NMR AND MOLECULAR MECHANICS CALCULATIONS [J].

CUNIASSE, P ;

SOWERS, LC ;

ERITJA, R ;

KAPLAN, B ;

GOODMAN, MF ;

COGNET, JAH ;

LEBRET, M ;

GUSCHLBAUER, W ;

FAZAKERLEY, GV .

NUCLEIC ACIDS RESEARCH, 1987, 15 (19) :8003-8022

[8] EXCISION OF URACIL RESIDUES IN DNA - MECHANISM OF ACTION OF ESCHERICHIA-COLI AND MICROCOCCUS-LUTEUS URACIL-DNA GLYCOSYLASES [J].

DELORT, AM ;

DUPLAA, AM ;

MOLKO, D ;

TEOULE, R ;

LEBLANC, JP ;

LAVAL, J .

NUCLEIC ACIDS RESEARCH, 1985, 13 (02) :319-335

[9]

Haines A. H., 1976, ADV CARBOHYD CHEM BI, V33, P11, DOI DOI 10.1016/S0065-2318(08)60280-

[10] ALKALINE DEGRADATION OF DEOXYRIBONUCLEIC ACID DERIVATIVES [J].

JONES, AS ;

MIAN, AM ;

WALKER, RT .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (16) :2042-&

← 1 2 3 →