Solid-phase synthesis of oligomeric deoxynucleic-thiourea (DNT) and deoxynucleic S-methylthiourea (DNmt):: a neutral/polycationic analogue of DNA

被引：14

作者：

Arya, DP ^{[1
]}

Bruice, TC ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 08期

关键词：

D O I：

10.1016/S0960-894X(00)00085-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A solid-phase synthesis for oligomeric DNmt is reported. Synthesis proceeds in 3'-5' direction and involves coupling of a protected 3'-isothiocyanate with the corresponding 5'-amine of the growing oligo chain. The difference in oligomeric thiourea/ S-methylthiourea binding to DNA is investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：691 / 693

页数：3

共 15 条

[1] Triple-helix formation of DNA oligomers with methylthiourea-linked nucleosides (DNmt): A kinetic and thermodynamic analysis [J].

Arya, DP ;

Bruice, TC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (08) :4384-4389

[2] Replacement of the negative phosphodiester linkages of DNA by positive S-methylthiourea linkers:: A novel approach to putative antisense agents [J].

Arya, DP ;

Bruice, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6619-6620

[3]

ARYA DP, 1998, J AM CHEM SOC, V120, P12

[4]

ATKINSON TD, 1990, ROY SOC CH, V80, P35

[5] Synthesis, biophysical properties, and nuclease resistance properties of mired backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: Deoxynucleic guanidine/DNA chimeras [J].

Barawkar, DA ;

Bruice, TC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (19) :11047-11052

[6] Antisense oligonucleotides: Is the glass half full or half empty? [J].

Bennett, CF .

BIOCHEMICAL PHARMACOLOGY, 1998, 55 (01) :9-19

[7] Association of short-strand DNA oligomers with guanidinium-linked nucleosides. A kinetic and thermodynamic study [J].

Blasko, A ;

Dempcy, RO ;

Minyat, EE ;

Bruice, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :7892-7899

[8] Fidelity of binding of the guanidinium nucleic acid (DNG) d(Tg)(4)-T-azido with short strand DNA oligomers (A(5)G(3)A(5), GA(4)G(3)A(4)G, G(2)A(3)G(3)A(3)G(2), G(2)A(2)G(5)A(2)G(2)). A kinetic and thermodynamic study [J].

Blasko, A ;

Minyat, EE ;

Dempcy, RO ;

Bruice, TC .

BIOCHEMISTRY, 1997, 36 (25) :7821-7831

[9] ANTISENSE OLIGODEOXYNUCLEOTIDES AS ANTIVIRAL AGENTS [J].

COHEN, JS .

ANTIVIRAL RESEARCH, 1991, 16 (02) :121-133

[10]

COOK PD, 1993, MED CHEM STRATEGIES

← 1 2 →