DEOXYRIBOSYLUREA AND DEOXYRIBOSYLFORMAMIDE OLIGONUCLEOTIDES

被引：9

作者：

BAILLET, S ^{[1
]}

BEHR, JP ^{[1
]}

机构：

[1] UNIV STRASBOURG 1, FAC PHARM STRASBOURG, CNRS, CHIM GENET LAB, F-67401 ILLKIRCH GRAFFENSTADEN, FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 49期

关键词：

D O I：

10.1016/0040-4039(95)01950-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triple helix-forming oligonucleotides could bind directly to natural B-DNA provided the sequence-recognition groups were directly linked to the ribose backbone. For adenine recognition, the a bonding network of a deoxyribosylamide is required. To this end, deoxyribosylurea and deoxyribosylformamide were obtained by oxydative degradation of thymine. The former compound was shown to be an untractable slow exchange mixture of anomers. beta-Deoxyribosylformamide (F), a 7/3 cis:trans mixture of isomers, was tritylated, phosphitylated and an oligonucleotide T(F)(8)T was synthesized and characterized.

引用

收藏

页码：8981 / 8984

页数：4

相关论文

共 12 条

[1] STABILITIES OF DOUBLE-STRAND AND TRIPLE-STRAND HELICAL NUCLEIC-ACIDS [J].

CHENG, YK ;

PETTITT, BM .

PROGRESS IN BIOPHYSICS & MOLECULAR BIOLOGY, 1992, 58 (03) :225-257

[2] THE FORMATION AND METABOLISM OF N-HYDROXYMETHYL COMPOUNDS .5. H-1 AND C-13 NMR-SPECTRA OF THE ROTATIONAL ISOMERS OF N-HYDROXYMETHYLAMIDES AND DERIVATIVES [J].

GATE, EN ;

HOOPER, DL ;

STEVENS, MFG ;

THREADGILL, MD ;

VAUGHAN, K .

MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (02) :78-82

[3] SOLUTION CONFORMATION OF AN OLIGONUCLEOTIDE CONTAINING A UREA DEOXYRIBOSE RESIDUE IN FRONT OF A THYMINE [J].

GERVAIS, V ;

GUY, A ;

TEOULE, R ;

FAZAKERLEY, GV .

NUCLEIC ACIDS RESEARCH, 1992, 20 (24) :6455-6460

[4] INHIBITION OF GENE-EXPRESSION BY TRIPLE HELIX-DIRECTED DNA CROSS-LINKING AT SPECIFIC SITES [J].

GRIGORIEV, M ;

PRASEUTH, D ;

GUIEYSSE, AL ;

ROBIN, P ;

THUONG, NT ;

HELENE, C ;

HARELBELLAN, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (08) :3501-3505

[5] INCORPORATION BY CHEMICAL SYNTHESIS AND CHARACTERIZATION OF DEOXYRIBOSYLFORMYLAMINE INTO DNA [J].

GUY, A ;

DUPLAA, AM ;

ULRICH, J ;

TEOULE, R .

NUCLEIC ACIDS RESEARCH, 1991, 19 (21) :5815-5820

[6] INSERTION OF THE FRAGILE 2'-DEOXYRIBOSYLUREA RESIDUE INTO OLIGODEOXYNUCLEOTIDES [J].

GUY, A ;

AHMAD, S ;

TEOULE, R .

TETRAHEDRON LETTERS, 1990, 31 (40) :5745-5748

[7] SEQUENCE-TARGETED CHEMICAL MODIFICATIONS OF NUCLEIC-ACIDS BY COMPLEMENTARY OLIGONUCLEOTIDES COVALENTLY LINKED TO PORPHYRINS [J].

LEDOAN, T ;

PERROUAULT, L ;

CHASSIGNOL, M ;

THUONG, NT ;

HELENE, C .

NUCLEIC ACIDS RESEARCH, 1987, 15 (21) :8643-8659

[8] SEQUENCE-SPECIFIC CLEAVAGE OF DOUBLE HELICAL DNA BY TRIPLE HELIX FORMATION [J].

MOSER, HE ;

DERVAN, PB .

SCIENCE, 1987, 238 (4827) :645-650

[9] APPLICATION OF 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE FOR INSITU PREPARATION OF DEOXYRIBONUCLEOSIDE PHOSPHORAMIDITES AND THEIR USE IN POLYMER-SUPPORTED SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES [J].

NIELSEN, J ;

TAAGAARD, M ;

MARUGG, JE ;

VANBOOM, JH ;

DAHL, O .

NUCLEIC ACIDS RESEARCH, 1986, 14 (18) :7391-7403

[10] SUGAR MODIFIED OLIGONUCLEOTIDES .1. CARBO-OLIGODEOXYNUCLEOTIDES AS POTENTIAL ANTISENSE AGENTS [J].

PERBOST, M ;

LUCAS, M ;

CHAVIS, C ;

POMPON, A ;

BAUMGARTNER, H ;

RAYNER, B ;

GRIENGL, H ;

IMBACH, JL .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 165 (02) :742-747