Dramatic effect of the anomeric configuration on the thermal stability of duplex formed between novel dodecathymidine phosphoramidate (P-NH2) and complementary DNA and RNA strands

被引：16

作者：

Peyrottes, S ^{[1
]}

Vasseur, JJ ^{[1
]}

Imbach, JL ^{[1
]}

Rayner, B ^{[1
]}

机构：

[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,UMR 5625,F-34095 MONTPELLIER 5,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 33期

关键词：

D O I：

10.1016/0040-4039(96)01250-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The inversion of the anomeric configuration of the sugar moieties of a dodecathymidine combined with the replacement of the phosphodiester backbone by non-ionic phosphoramidate (P-NH2) produce a novel oligonucleotide analogue exhibiting unexpected high affinity for DNA and RNA targets. In comparison the phosphoramidate oligomer with the natural sugar anomer binds much less efficiently. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：5869 / 5872

页数：4

共 20 条

[1] OXALYL-CPG - A LABILE SUPPORT FOR SYNTHESIS OF SENSITIVE OLIGONUCLEOTIDE DERIVATIVES [J].

ALUL, RH ;

SINGMAN, CN ;

ZHANG, GR ;

LETSINGER, RL .

NUCLEIC ACIDS RESEARCH, 1991, 19 (07) :1527-1532

[2] RATE OF DEGRADATION OF [ALPHA]-OLIGODEOXYNUCLEOTIDES AND [BETA]-OLIGODEOXYNUCLEOTIDES IN XENOPUS OOCYTES - IMPLICATIONS FOR ANTI-MESSENGER STRATEGIES [J].

CAZENAVE, C ;

CHEVRIER, M ;

THUONG, NT ;

HELENE, C .

NUCLEIC ACIDS RESEARCH, 1987, 15 (24) :10507-10521

[3]

CROOKES ST, 1993, ANTISENSE RES APPL

[4] DEOXYNUCLEOSIDE H-PHOSPHONATE DIESTER INTERMEDIATES IN THE SYNTHESIS OF INTERNUCLEOTIDE PHOSPHATE ANALOGS [J].

FROEHLER, BC .

TETRAHEDRON LETTERS, 1986, 27 (46) :5575-5578

[5] SYNTHESIS OF DNA VIA DEOXYNUCLEOSIDE H-PHOSPHONATE INTERMEDIATES [J].

FROEHLER, BC ;

NG, PG ;

MATTEUCCI, MD .

NUCLEIC ACIDS RESEARCH, 1986, 14 (13) :5399-5407

[6] ALPHA-DNA .9. PARALLEL ANNEALING OF ALPHA-ANOMERIC OLIGODEOXYRIBONUCLEOTIDES TO NATURAL MESSENGER-RNA IS REQUIRED FOR INTERFERENCE IN RNASE-H MEDIATED HYDROLYSIS AND REVERSE TRANSCRIPTION [J].

GAGNOR, C ;

RAYNER, B ;

LEONETTI, JP ;

IMBACH, JL ;

LEBLEU, B .

NUCLEIC ACIDS RESEARCH, 1989, 17 (13) :5107-5114

[7]

GAREGG PJ, 1986, CHEM SCRIPTA, V26, P59

[8] CURRENT CONCEPTS IN ANTISENSE DRUG DESIGN [J].

MILLIGAN, JF ;

MATTEUCCI, MD ;

MARTIN, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (14) :1923-1937

[9] ALPHA-DNA-V - PARALLEL ANNEALING, HANDEDNESS AND CONFORMATION OF THE DUPLEX OF THE UNNATURAL ALPHA-HEXADEOXYRIBONUCLEOTIDE ALPHA-[D(CPAPTPGPCPG)] WITH ITS BETA-COMPLEMENT BETA-[D(GPTPAPCPGPC)] DEDUCED FROM HIGH-FIELD H-1-NMR [J].

MORVAN, F ;

RAYNER, B ;

IMBACH, JL ;

LEE, M ;

HARTLEY, JA ;

CHANG, DK ;

LOWN, JW .

NUCLEIC ACIDS RESEARCH, 1987, 15 (17) :7027-7044

[10] ALPHA-DNA .1. SYNTHESIS, CHARACTERIZATION BY HIGH-FIELD H-1-NMR, AND BASE-PAIRING PROPERTIES OF THE UNNATURAL HEXADEOXYRIBONUCLEOTIDE ALPHA-[D(CPCPTPTPCPC)] WITH ITS COMPLEMENT BETA-[D(GPGPAPAPGPG)] [J].

MORVAN, F ;

RAYNER, B ;

IMBACH, JL ;

CHANG, DK ;

LOWN, JW .

NUCLEIC ACIDS RESEARCH, 1986, 14 (12) :5019-5035

← 1 2 →