Synthesis and adduction of fully deprotected oligodeoxynucleotides containing 6-chloropurine

被引：15

作者：

Kim, HY

Nechev, L

Zhou, LA

Tamura, P

Harris, CM

Harris, TM

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37232 USA

[2] Vanderbilt Univ, Ctr Mol Toxicol, Nashville, TN 37232 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 38期

关键词：

nucleosides; nucleic acids; purines;

D O I：

10.1016/S0040-4039(98)01462-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fully deprotected oligodeoxynucleotides containing 6-chloropurine have been synthesized and used in solution phase reactions with amine nucleophiles to prepare oligonucleotides containing substituted adenine residues. This strategy was used for the preparation of a double-stranded oligonucleotide crosslinked by a 4-carbon tether between N-6 positions of deoxyadenosines in the two strands. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6803 / 6806

页数：4

相关论文

共 24 条

[11] NITROGEN-15-LABELED DEOXYNUCLEOSIDES - SYNTHESIS OF [6-N-15]-DEOXYADENOSINES AND [1-N-15]DEOXYADENOSINES FROM DEOXYADENOSINE [J].

GAO, X ;

JONES, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1275-1278

[12] NEW STRATEGY FOR THE SYNTHESIS OF OLIGODEOXYNUCLEOTIDES BEARING ADDUCTS AT EXOCYCLIC AMINO SITES OF PURINE NUCLEOSIDES [J].

HARRIS, CM ;

ZHOU, L ;

STRAND, EA ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4328-4329

[13] A POSTOLIGOMERIZATION SYNTHESIS OF OLIGODEOXYNUCLEOTIDES CONTAINING POLYCYCLIC AROMATIC HYDROCARBON ADDUCTS AT THE N(6) POSITION OF DEOXYADENOSINE [J].

KIM, SJ ;

STONE, MP ;

HARRIS, CM ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5480-5481

[14] AN EFFICIENT ROUTE TO N-6 DEOXYADENOSINE ADDUCTS OF DIOL EPOXIDES OF CARCINOGENIC POLYCYCLIC AROMATIC-HYDROCARBONS [J].

KIM, SJ ;

JAJOO, HK ;

KIM, HY ;

ZHOU, L ;

HORTON, P ;

HARRIS, CM ;

HARRIS, TM .

BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (06) :811-822

[15] N-ACYL PROTECTING GROUPS FOR DEOXYNUCLEOSIDES - A QUANTITATIVE AND COMPARATIVE-STUDY [J].

KOSTER, H ;

KULIKOWSKI, K ;

LIESE, T ;

HEIKENS, W ;

KOHLI, V .

TETRAHEDRON, 1981, 37 (02) :363-369

[16] ENGINEERING TETHERED DNA-MOLECULES BY THE CONVERTIBLE NUCLEOSIDE APPROACH [J].

MACMILLAN, AM ;

VERDINE, GL .

TETRAHEDRON, 1991, 47 (14-15) :2603-2616

[17] SYNTHESIS AND CROSS-LINKING PROPERTIES OF A DEOXYOLIGONUCLEOTIDE CONTAINING N6,N6-ETHANODEOXYADENOSINE [J].

MATTEUCCI, MD ;

WEBB, TR .

TETRAHEDRON LETTERS, 1987, 28 (22) :2469-2472

[18] UTILITY OF PURINYL RADICALS IN THE SYNTHESIS OF BASE-MODIFIED NUCLEOSIDES AND ALKYLPURINES - 6-AMINO GROUP REPLACEMENT BY H, CL, BR, AND I [J].

NAIR, V ;

RICHARDSON, SG .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :3969-3974

[19] REMARKABLE ENHANCEMENT OF BINDING-AFFINITY OF HETEROCYCLE-MODIFIED DNA TO DNA AND RNA - SYNTHESIS, CHARACTERIZATION AND BIOPHYSICAL EVALUATION OF N-2-IMIDAZOLYLPROPYLGUANINE AND N-2-IMIDAZOLYLPROPYL-2-AMINOADENINE MODIFIED OLIGONUCLEOTIDES [J].

RAMASAMY, KS ;

ZOUNES, M ;

GONZALEZ, C ;

FREIER, SM ;

LESNIK, EA ;

CUMMINS, LL ;

GRIFFEY, RH ;

MONIA, BP ;

COOK, PD .

TETRAHEDRON LETTERS, 1994, 35 (02) :215-218

[20]

ROBINS MJ, 1978, NUCLEIC ACID CHEM, P601