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.

引用

页码：3555 / 3558

页数：4

共 20 条

[1] PREPARATION OF THE 8,9-EPOXIDE OF THE MYCOTOXIN AFLATOXIN-B1 - THE ULTIMATE CARCINOGENIC SPECIES
BAERTSCHI, SW
RANEY, KD
STONE, MP
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7929 - 7931
[2] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES
BANNWARTH, W
TRZECIAK, A
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (01) : 175 - 186
[3] INSITU ACTIVATION OF BIS-DIALKYLAMINOPHOSPHINES - A NEW METHOD FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES ON POLYMER SUPPORTS
BARONE, AD
TANG, JY
CARUTHERS, MH
[J]. 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)
COSMAN, M
IBANEZ, V
GEACINTOV, NE
HARVEY, RG
[J]. 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
Custer, L
Zajc, B
Sayer, JM
Cullinane, C
Phillips, DR
Cheh, AM
Jerina, DM
Bohr, VA
Mazur, SJ
[J]. 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
Edwards, C
Boche, G
Steinbrecher, T
Scheer, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1887 - 1893
[8] SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 2'-DEOXYNEBULARINE AND 2'-DEOXYXANTHOSINE
ERITJA, R
HOROWITZ, DM
WALKER, PA
ZIEHLERMARTIN, JP
BOOSALIS, MS
GOODMAN, MF
ITAKURA, K
KAPLAN, BE
[J]. 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
HARRIS, CM
ZHOU, L
STRAND, EA
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) : 4328 - 4329
[10] HARRIS TM, 1994, POLYCYCL AROMAT COMP, V6, P9, DOI 10.1080/10406639408031162

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