Synthesis and hybridization property of an oligonucleotide analog containing 1′,3′-di-O-methylene-α-D-fructose backbone

被引：4

作者：

Zou, RM ^{[1
]}

Matteucci, MD ^{[1
]}

机构：

[1] Gilead Sci Inc, Foster City, CA 94404 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 21期

关键词：

D O I：

10.1016/S0960-894X(98)00566-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Hydrogen phosphonate monomers of T (thymine) and C-m (5-methylcytosine) bearing a 1',3'-di-O-methylene-alpha-D-fructose sugar moiety were synthesized and incorporated into an oligonucleotide. Hybridization studies by thermal denaturation experiment indicated that this oligonucleotide did not form a duplex with the complementary RNA target. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

引用

收藏

页码：3049 / 3052

页数：4

相关论文

共 14 条

[1] SYNTHESIS OF D-FRUCTOFURANOSYLPURINE NUCLEOSIDES [J].

BOUALI, A ;

EWING, DF ;

MACKENZIE, G .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1994, 13 (1-3) :491-499

[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] THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE) [J].

CRAM, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08) :1009-1020

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

FROEHLER, BC ;

NG, PG ;

MATTEUCCI, MD .

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

[5] MEDICINAL CHEMISTRY IN THE GOLDEN-AGE OF BIOLOGY - LESSONS FROM STEROID AND PEPTIDE RESEARCH [J].

HIRSCHMANN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (10) :1278-1301

[6] OLIGONUCLEOTIDES CONTAINING A COVALENT CONFORMATIONALLY RESTRICTED PHOSPHODIESTER ANALOG FOR HIGH-AFFINITY TRIPLE-HELIX FORMATION - THE RIBOACETAL INTERNUCLEOTIDE LINKAGE [J].

JONES, RJ ;

SWAMINATHAN, S ;

MILLIGAN, JF ;

WADWANI, S ;

FROEHLER, BC ;

MATTEUCCI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9816-9817

[7] SUPRAMOLECULAR CHEMISTRY - SCOPE AND PERSPECTIVES MOLECULES, SUPERMOLECULES, AND MOLECULAR DEVICES [J].

LEHN, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (01) :89-112

[8] ALPHA-DNA-II - SYNTHESIS OF UNNATURAL ALPHA-ANOMERIC OLIGODEOXYRIBONUCLEOTIDES CONTAINING THE 4 USUAL BASES AND STUDY OF THEIR SUBSTRATE ACTIVITIES FOR NUCLEASES [J].

MORVAN, F ;

RAYNER, B ;

IMBACH, JL ;

THENET, S ;

BERTRAND, JR ;

PAOLETTI, J ;

MALVY, C ;

PAOLETTI, C .

NUCLEIC ACIDS RESEARCH, 1987, 15 (08) :3421-3437

[9] 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 [J].

Peyrottes, S ;

Vasseur, JJ ;

Imbach, JL ;

Rayner, B .

TETRAHEDRON LETTERS, 1996, 37 (33) :5869-5872

[10]

SAENGER W, 1984, PRINCIPLES NUCL ACID, P57