Synthesis of oligonucleotides containing bulky adducts at guanine N2 via the phosphoramidite of O2-triflate-O6-NPE 2′-deoxyxanthosine

被引：22

作者：

Cooper, MD

Hodge, RP

Tamura, PJ

Wilkinson, AS

Harris, CM

Harris, TM

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

[2] Vanderbilt Univ, Ctr Mol Toxicol, Nashville, TN 37235 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

关键词：

nucleic acids; nucleosides; polycyclic aromatic compounds; purines;

D O I：

10.1016/S0040-4039(00)00461-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oligodeoxynucleotides bearing bulky adducts at guanine N-2 have been prepared by a postoligomerization strategy in which oligonucleotides containing a highly reactive O-2-trifluoromethanesuIfonyl-O-6-(p-nitrophenethyl) 2'-deoxyxanthosine residue were reacted with (+/-)-10 beta-amino-7,8,9,10-tetrahydro-benzo[a]pyrene-7 beta,8 alpha,9 alpha-triol and related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：3555 / 3558

页数：4

相关论文

共 20 条

[1] PREPARATION OF THE 8,9-EPOXIDE OF THE MYCOTOXIN AFLATOXIN-B1 - THE ULTIMATE CARCINOGENIC SPECIES [J].

BAERTSCHI, SW ;

RANEY, KD ;

STONE, MP ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7929-7931

[2] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES [J].

BANNWARTH, W ;

TRZECIAK, A .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :175-186

[3] INSITU ACTIVATION OF BIS-DIALKYLAMINOPHOSPHINES - A NEW METHOD FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES ON POLYMER SUPPORTS [J].

BARONE, AD ;

TANG, JY ;

CARUTHERS, MH .

NUCLEIC ACIDS RESEARCH, 1984, 12 (10) :4051-4061

[4]

BUCHI G, 1982, J AM CHEM SOC, V104, P544, DOI 10.1021/ja00366a029

[5] PREPARATION AND ISOLATION OF ADDUCTS IN HIGH-YIELD DERIVED FROM THE BINDING OF 2 BENZO[A]PYRENE-7,8-DIHYDROXY-9,10-OXIDE STEREOISOMERS TO THE OLIGONUCLEOTIDE D(ATATGTATA) [J].

COSMAN, M ;

IBANEZ, V ;

GEACINTOV, NE ;

HARVEY, RG .

CARCINOGENESIS, 1990, 11 (09) :1667-1672

[6] Stereospecific differences in repair by human cell extracts of synthesized oligonucleotides containing trans-opened 7,8,9,10-tetrahydrobenzo[a]pyrene-7,8-diol-9,10-epoxide-N2-dG adduct stereoisomers located within the human K-ras codon 12 sequence [J].

Custer, L ;

Zajc, B ;

Sayer, JM ;

Cullinane, C ;

Phillips, DR ;

Cheh, AM ;

Jerina, DM ;

Bohr, VA ;

Mazur, SJ .

BIOCHEMISTRY, 1999, 38 (02) :569-581

[7] Synthesis of 2-substituted 2'-deoxyguanosines and 6-O-allylguanines via the activation of C-2 by a trifluoromethanesulfonate group [J].

Edwards, C ;

Boche, G ;

Steinbrecher, T ;

Scheer, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12) :1887-1893

[8] SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 2'-DEOXYNEBULARINE AND 2'-DEOXYXANTHOSINE [J].

ERITJA, R ;

HOROWITZ, DM ;

WALKER, PA ;

ZIEHLERMARTIN, JP ;

BOOSALIS, MS ;

GOODMAN, MF ;

ITAKURA, K ;

KAPLAN, BE .

NUCLEIC ACIDS RESEARCH, 1986, 14 (20) :8135-8153

[9] 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

[10]

HARRIS TM, 1994, POLYCYCL AROMAT COMP, V6, P9, DOI 10.1080/10406639408031162