6-VINYLATED GUANOSINE AS A NOVEL CROSS-LINKING AGENT AND ITS VERSATILE SYNTHESIS FROM THE 6-O-TOSYLATE BY PD(0)-CATALYZED CROSS-COUPLING

被引：74

作者：

NAGATSUGI, F ^{[1
]}

UEMURA, K ^{[1
]}

NAKASHIMA, S ^{[1
]}

MAEDA, M ^{[1
]}

SASAKI, S ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,HIGASHI KU,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 03期

关键词：

D O I：

10.1016/0040-4039(94)02224-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Vinylated guanosine(1) was designed as a novel cross-linking agent, and synthesized by a new Pd(O)-catalyzed cross-coupling reaction using guanosine 6-Otosylate and vinyltributylstannane. Its potential as a cross-linking agent was demonstrated by adduct formation with guanosine and cytidine at the 7-N and 4-N positions, respectively.

引用

页码：421 / 424

页数：4

共 18 条

[1] SEQUENCE-SPECIFIC CLEAVAGE OF DNA BY N-BROMOACETYLDISTAMYCIN - PRODUCT AND KINETIC ANALYSES [J].

BAKER, BF ;

DERVAN, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2700-2712

[2] THE FUNCTIONALIZATION OF OLIGONUCLEOTIDES VIA PHOSPHORAMIDITE DERIVATIVES [J].

BEAUCAGE, SL ;

IYER, RP .

TETRAHEDRON, 1993, 49 (10) :1925-1963

[3] THE ROLE OF A QUINONE METHIDE IN THE SEQUENCE-SPECIFIC ALKYLATION OF DNA [J].

CHATTERJEE, M ;

ROKITA, SE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1690-1697

[4] A NOVEL COMBINED CHEMICAL ENZYMATIC-SYNTHESIS OF CROSS-LINKED DNA USING A NUCLEOSIDE TRIPHOSPHATE ANALOG [J].

COWART, M ;

BENKOVIC, SJ .

BIOCHEMISTRY, 1991, 30 (03) :788-796

[5] 6-CHLOROPURINES AND ORGANOSTANNANES IN PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS [J].

GUNDERSEN, LL .

TETRAHEDRON LETTERS, 1994, 35 (19) :3155-3158

[6] RATIONAL DESIGN OF SEQUENCE-SPECIFIC DNA LIGANDS FOR ARTIFICIAL CONTROL OF GENE-EXPRESSION [J].

HELENE, C .

PURE AND APPLIED CHEMISTRY, 1994, 66 (04) :663-669

[7] ACIDIC DOMAINS AROUND NUCLEIC-ACIDS [J].

LAMM, G ;

PACK, GR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (22) :9033-9036

[8] PHOSPHORODITHIOATE DNA AS A POTENTIAL THERAPEUTIC DRUG [J].

MARSHALL, WS ;

CARUTHERS, MH .

SCIENCE, 1993, 259 (5101) :1564-1569

[9] EFFICIENT, SPECIFIC CROSS-LINKING AND CLEAVAGE OF DNA BY STABLE, SYNTHETIC COMPLEMENTARY OLIGODEOXYNUCLEOTIDES [J].

MEYER, RB ;

TABONE, JC ;

HURST, GD ;

SMITH, TM ;

GAMPER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8517-8519

[10] SEQUENCE-SPECIFIC DOUBLE-STRAND ALKYLATION AND CLEAVAGE OF DNA MEDIATED BY TRIPLE-HELIX FORMATION [J].

POVSIC, TJ ;

STROBEL, SA ;

DERVAN, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5934-5941

← 1 2 →