MILD ACID-HYDROLYSIS OF 2-PYRIMIDINONE-CONTAINING DNA FRAGMENTS GENERATES APURINIC APYRIMIDINIC SITES

被引：33

作者：

IOCONO, JA ^{[1
]}

GILDEA, B ^{[1
]}

MCLAUGHLIN, LW ^{[1
]}

机构：

[1] BOSTON COLL, DEPT CHEM, CHESTNUT HILL, MA 02167 USA

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)94363-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile glycosidic bond cleavage of 2-pyrimidinone-2′-deoxynucleosides occurs under mildly acidic conditions (pH 3.0) and ambient temperature. When a 2-pyrimidinone nucleoside residue is present in a DNA fragment, hydrolysis results in an apurinic/apyrimidinic (abasic) site. The incorporation of 2-pyrimidinones into chemically synthesized DNA provides a route for the chemical generation of an abasic site at a preselected position in the sequence. © 1990.

引用

页码：175 / 178

页数：4

共 18 条

[1] AN ABASIC SITE IN DNA - SOLUTION CONFORMATION DETERMINED BY PROTON NMR AND MOLECULAR MECHANICS CALCULATIONS
CUNIASSE, P
SOWERS, LC
ERITJA, R
KAPLAN, B
GOODMAN, MF
COGNET, JAH
LEBRET, M
GUSCHLBAUER, W
FAZAKERLEY, GV
[J]. NUCLEIC ACIDS RESEARCH, 1987, 15 (19) : 8003 - 8022
[2] ESTIMATION OF APURINIC-APYRIMIDINIC SITES AND PHOSPHOTRIESTERS IN DEOXYRIBONUCLEIC-ACID TREATED WITH ELECTROPHILIC CARCINOGENS AND MUTAGENS
DRINKWATER, NR
MILLER, EC
MILLER, JA
[J]. BIOCHEMISTRY, 1980, 19 (22) : 5087 - 5092
[3] SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING THE ABASIC SITE MODEL-COMPOUND 1,4-ANHYDRO-2-DEOXY-D-RIBITOL
ERITJA, R
WALKER, PA
RANDALL, SK
GOODMAN, MF
KAPLAN, BE
[J]. NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (04): : 803 - 814
[4] LOSS OF AN APURINIC APYRIMIDINIC SITE ENDONUCLEASE INCREASES THE MUTAGENICITY OF N-METHYL-N'-NITRO-N-NITROSOGUANIDINE TO ESCHERICHIA-COLI
FOSTER, PL
DAVIS, EF
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (09) : 2891 - 2895
[5] THE SYNTHESIS OF 2-PYRIMIDINONE NUCLEOSIDES AND THEIR INCORPORATION INTO OLIGODEOXYNUCLEOTIDES
GILDEA, B
MCLAUGHLIN, LW
[J]. NUCLEIC ACIDS RESEARCH, 1989, 17 (06) : 2261 - 2281
[6] GREER SHELDON, 1962, JOUR MOLECULAR BIOL, V4, P123
[7] NMR-STUDIES OF ABASIC SITES IN DNA DUPLEXES - DEOXYADENOSINE STACKS INTO THE HELIX OPPOSITE THE CYCLIC ANALOG OF 2-DEOXYRIBOSE
KALNIK, MW
CHANG, CN
GROLLMAN, AP
PATEL, DJ
[J]. BIOCHEMISTRY, 1988, 27 (03) : 924 - 931
[8] Lindahl T, 1979, Prog Nucleic Acid Res Mol Biol, V22, P135
[9] RATE OF DEPURINATION OF NATIVE DEOXYRIBONUCLEIC ACID
LINDAHL, T
NYBERG, B
[J]. BIOCHEMISTRY, 1972, 11 (19) : 3610 - &
[10] MUTAGENESIS BY APURINIC APYRIMIDINIC SITES
LOEB, LA
PRESTON, BD
[J]. ANNUAL REVIEW OF GENETICS, 1986, 20 : 201 - 230

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