AN IMPROVED METHOD FOR THE PREPARATION OF THE PHOSPHORAMIDITES OF MODIFIED 2'-DEOXYNUCLEOTIDES - INCORPORATION OF 8-OXO-2'-DEOXY-7H-GUANOSINE INTO SYNTHETIC OLIGOMERS

被引:55
作者
BODEPUDI, V
IDEN, CR
JOHNSON, F
机构
[1] Department of Pharmacological Sciences, School of Medicine, Health Sciences Center, State University of New York at Stony Brook, Stony Brook
基金
美国国家卫生研究院;
关键词
D O I
10.1080/07328319108046660
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
3'-O-(Diisopropylamino-2-cyanoethoxyphosphinyl)-5'-O-(4,4'-dimethoxytrityl)-N2-isobutyryl-8-oxo-2'-deoxy-7H-guanosine (7) was synthesized and used for the introduction of an 8-oxo-2'-deoxy-7H-guanosine residue into a DNA oligomer by means of automated synthesis. A modification of the preparation of the phosphoramidite markedly improves the coupling efficiency in the oligomer synthesis in this and several other cases that were tested.
引用
收藏
页码:755 / 761
页数:7
相关论文
共 24 条
[1]   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
[2]   DEOXYNUCLEOSIDE PHOSPHORAMIDITES - A NEW CLASS OF KEY INTERMEDIATES FOR DEOXYPOLYNUCLEOTIDE SYNTHESIS [J].
BEAUCAGE, SL ;
CARUTHERS, MH .
TETRAHEDRON LETTERS, 1981, 22 (20) :1859-1862
[3]   SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING THE ABASIC SITE MODEL-COMPOUND 1,4-ANHYDRO-2-DEOXY-D-RIBITOL [J].
ERITJA, R ;
WALKER, PA ;
RANDALL, SK ;
GOODMAN, MF ;
KAPLAN, BE .
NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (04) :803-814
[4]   PURINE NUCLEOSIDES .9. SYNTHESIS OF 9-BETA-D-RIBOFURANOSYL URIC ACID AND OTHER RELATED 8-SUBSTITUTED PURINE RIBONUCLEOSIDES [J].
HOLMES, RE ;
ROBINS, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (08) :1772-&
[5]   8-HYDROXYDEOXYGUANOSINE IN DNA INHIBITS RESTRICTION ENDONUCLEASE DIGESTION [J].
JONES, DS ;
NEMOTO, F ;
KUCHINO, Y ;
OHTSUKA, E ;
NISHIMURA, S .
NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (02) :223-233
[6]  
KARPYSHEV NN, 1988, RUSS CHEM REV, V57, P886
[7]   HYDROXYLATION OF DEOXYGUANOSINE AT THE C-8 POSITION BY ASCORBIC-ACID AND OTHER REDUCING AGENTS [J].
KASAI, H ;
NISHIMURA, S .
NUCLEIC ACIDS RESEARCH, 1984, 12 (04) :2137-2145
[8]   FORMATION OF 8-HYDROXYGUANINE MOIETY IN CELLULAR DNA BY AGENTS PRODUCING OXYGEN RADICALS AND EVIDENCE FOR ITS REPAIR [J].
KASAI, H ;
CRAIN, PF ;
KUCHINO, Y ;
NISHIMURA, S ;
OOTSUYAMA, A ;
TANOOKA, H .
CARCINOGENESIS, 1986, 7 (11) :1849-1851
[9]  
KASAI H, 1984, JPN J CANCER RES, V75, P1037
[10]  
KASAI H, 1984, JPN J CANCER RES, V75, P565