Misincorporation of dNTPs Opposite 1,N2-Ethenoguanine and 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine in Oligonucleotides by Escherichia coli Polymerases I exo- and II exo-, T7 Polymerase exo-, Human Immunodeficiency Virus-1 Reverse Transcriptase, and Rat Polymerase β†
Identifieur interne : 003C60 ( Main/Exploration ); précédent : 003C59; suivant : 003C61Misincorporation of dNTPs Opposite 1,N2-Ethenoguanine and 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine in Oligonucleotides by Escherichia coli Polymerases I exo- and II exo-, T7 Polymerase exo-, Human Immunodeficiency Virus-1 Reverse Transcriptase, and Rat Polymerase β†
Auteurs : Sophie Langouët [États-Unis] ; Michael Müller [États-Unis, Allemagne] ; F. Peter Guengerich [États-Unis]Source :
- Biochemistry [ 0006-2960 ] ; 1997.
Descripteurs français
- KwdFr :
- Cancérogènes (métabolisme), DNA-directed DNA polymerase (métabolisme), Désoxyribonucléotides (), Désoxyribonucléotides (métabolisme), Guanine (), Guanine (analogues et dérivés), Guanine (métabolisme), Imidazoles (), Imidazoles (métabolisme), Mutagenèse, Nucléotide désoxyadenylique (métabolisme), Nucléotide désoxyguanylique (métabolisme), Oligodésoxyribonucléotides (biosynthèse), Purines (), Purines (métabolisme), Transcription génétique.
- MESH :
- analogues et dérivés : Guanine.
- biosynthèse : Oligodésoxyribonucléotides.
- métabolisme : Cancérogènes, DNA-directed DNA polymerase, Désoxyribonucléotides, Guanine, Imidazoles, Nucléotide désoxyadenylique, Nucléotide désoxyguanylique, Purines.
- Désoxyribonucléotides, Guanine, Imidazoles, Mutagenèse, Purines, Transcription génétique.
English descriptors
- KwdEn :
- Carcinogens (metabolism), DNA-Directed DNA Polymerase (metabolism), Deoxyadenine Nucleotides (metabolism), Deoxyguanine Nucleotides (metabolism), Deoxyribonucleotides (chemistry), Deoxyribonucleotides (metabolism), Guanine (analogs & derivatives), Guanine (chemistry), Guanine (metabolism), Imidazoles (chemistry), Imidazoles (metabolism), Mutagenesis, Oligodeoxyribonucleotides (biosynthesis), Purines (chemistry), Purines (metabolism), Transcription, Genetic.
- MESH :
- chemical , analogs & derivatives : Guanine.
- chemical , biosynthesis : Oligodeoxyribonucleotides.
- chemical , chemistry : Deoxyribonucleotides, Guanine, Imidazoles, Purines.
- chemical , metabolism : Carcinogens, DNA-Directed DNA Polymerase, Deoxyadenine Nucleotides, Deoxyguanine Nucleotides, Deoxyribonucleotides, Guanine, Imidazoles, Purines.
- Mutagenesis, Transcription, Genetic.
Abstract
1,N2-Ethenoguanine (1,N2-ε-Gua) and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine (HO-ethanoGua) are two modified bases formed in the reaction of DNA with 2-chlorooxirane, the epoxide derivative of vinyl chloride. The oligonucleotides (19-mers), 5‘-CAGTGGGTG*TCCGAATTGA-3‘, were prepared, with each of these modified bases substituted for G at G*. HO-ethanodeoxyguanosine exists predominantly as a mixture of diastereomers of the closed cyclic hemiaminal form, 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine, shown by H218O experiments to be in equilibrium with the open form, N2-(2-oxoethyl)Gua. Both adducts retarded the 3‘-extension of a complementary 10-mer primer by all of the polymerases examined, but in every case, some full-length product was obtained. Nucleotide sequence analysis indicated misincorporation of dGTP and dATP across from both 1,N2-ε-Gua and HO-ethanoGua, with the extent varying considerably among the polymerases. Similar results were obtained when the abilities of the polymerases to incorporate a single dNTP were evaluated. In addition, −1 and −2 base frame shifts were detected with both 1,N2-ε-Gua and HO-ethanoGua with some of the polymerases. Steady-state kinetic experiments with Escherichia coli polymerase I exo- and T7 polymerase exo-/thioredoxin showed large decreases in kcat for all dNTP incorporations compared to the normal G·dCTP pair and high misincorporation frequencies for dATP and dGTP with both adducts (compared to dCTP). Collectively, the results indicate that both of these adducts have considerable miscoding potential with some of these polymerases, that there are a number of differences between the 1,N2-ε-Gua and HO-ethanoGua adducts (which formally differ only in the presence of the elements of water), and that misincorporation of dNTPs at a single modified base can vary considerably among different polymerases even in the absence of exonuclease activity.
Url:
DOI: 10.1021/bi962526v
Affiliations:
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5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-<hi rend="italic">a</hi>]purine in Oligonucleotides by
<hi rend="italic">Escherichia coli</hi> Polymerases I exo<hi rend="superscript">-</hi> and II exo<hi rend="superscript">-</hi>, T7 Polymerase exo<hi rend="superscript">-</hi>, Human
Immunodeficiency Virus-1 Reverse Transcriptase, and Rat Polymerase β<ref type="bib" target="#bi962526vAF2"><hi rend="superscript">†</hi></ref></title><author><name sortKey="Langouet, Sophie" sort="Langouet, Sophie" uniqKey="Langouet S" first="Sophie" last="Langouët">Sophie Langouët</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation></author><author><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation><affiliation wicri:level="4"><country xml:lang="fr">Allemagne</country><wicri:regionArea> Current address: Abt. Arbeits-und Sozialmedizinder Georg-August-Universität Göttingen, Waldweg 37, D-37073Göttingen</wicri:regionArea><placeName><region type="land" nuts="2">Basse-Saxe</region><settlement type="city">Göttingen</settlement></placeName><orgName type="university">Université de Göttingen</orgName></affiliation></author><author><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation><affiliation wicri:level="1"><country wicri:rule="url">États-Unis</country></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Biochemistry</title><title level="j" type="abbrev">Biochemistry</title><idno type="ISSN">0006-2960</idno><idno type="eISSN">1520-4995</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published">1997</date><date type="published">1997</date><biblScope unit="vol">36</biblScope><biblScope unit="issue">20</biblScope><biblScope unit="page" from="6069">6069</biblScope><biblScope unit="page" to="6079">6079</biblScope></imprint><idno type="ISSN">0006-2960</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0006-2960</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Carcinogens (metabolism)</term><term>DNA-Directed DNA Polymerase (metabolism)</term><term>Deoxyadenine Nucleotides (metabolism)</term><term>Deoxyguanine Nucleotides (metabolism)</term><term>Deoxyribonucleotides (chemistry)</term><term>Deoxyribonucleotides (metabolism)</term><term>Guanine (analogs & derivatives)</term><term>Guanine (chemistry)</term><term>Guanine (metabolism)</term><term>Imidazoles (chemistry)</term><term>Imidazoles (metabolism)</term><term>Mutagenesis</term><term>Oligodeoxyribonucleotides (biosynthesis)</term><term>Purines (chemistry)</term><term>Purines (metabolism)</term><term>Transcription, Genetic</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Cancérogènes (métabolisme)</term><term>DNA-directed DNA polymerase (métabolisme)</term><term>Désoxyribonucléotides ()</term><term>Désoxyribonucléotides (métabolisme)</term><term>Guanine ()</term><term>Guanine (analogues et dérivés)</term><term>Guanine (métabolisme)</term><term>Imidazoles ()</term><term>Imidazoles (métabolisme)</term><term>Mutagenèse</term><term>Nucléotide désoxyadenylique (métabolisme)</term><term>Nucléotide désoxyguanylique (métabolisme)</term><term>Oligodésoxyribonucléotides (biosynthèse)</term><term>Purines ()</term><term>Purines (métabolisme)</term><term>Transcription génétique</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Guanine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Deoxyribonucleotides</term><term>Guanine</term><term>Imidazoles</term><term>Purines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Carcinogens</term><term>DNA-Directed DNA Polymerase</term><term>Deoxyadenine Nucleotides</term><term>Deoxyguanine Nucleotides</term><term>Deoxyribonucleotides</term><term>Guanine</term><term>Imidazoles</term><term>Purines</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Guanine</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>Oligodésoxyribonucléotides</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Cancérogènes</term><term>DNA-directed DNA polymerase</term><term>Désoxyribonucléotides</term><term>Guanine</term><term>Imidazoles</term><term>Nucléotide désoxyadenylique</term><term>Nucléotide désoxyguanylique</term><term>Purines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Mutagenesis</term><term>Transcription, Genetic</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Désoxyribonucléotides</term><term>Guanine</term><term>Imidazoles</term><term>Mutagenèse</term><term>Purines</term><term>Transcription génétique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract">1,N2-Ethenoguanine (1,N2-ε-Gua) and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine (HO-ethanoGua) are two modified bases formed in the reaction of DNA with 2-chlorooxirane, the epoxide derivative of vinyl chloride. The oligonucleotides (19-mers), 5‘-CAGTGGGTG*TCCGAATTGA-3‘, were prepared, with each of these modified bases substituted for G at G*. HO-ethanodeoxyguanosine exists predominantly as a mixture of diastereomers of the closed cyclic hemiaminal form, 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine, shown by H218O experiments to be in equilibrium with the open form, N2-(2-oxoethyl)Gua. Both adducts retarded the 3‘-extension of a complementary 10-mer primer by all of the polymerases examined, but in every case, some full-length product was obtained. Nucleotide sequence analysis indicated misincorporation of dGTP and dATP across from both 1,N2-ε-Gua and HO-ethanoGua, with the extent varying considerably among the polymerases. Similar results were obtained when the abilities of the polymerases to incorporate a single dNTP were evaluated. In addition, −1 and −2 base frame shifts were detected with both 1,N2-ε-Gua and HO-ethanoGua with some of the polymerases. Steady-state kinetic experiments with Escherichia coli polymerase I exo- and T7 polymerase exo-/thioredoxin showed large decreases in kcat for all dNTP incorporations compared to the normal G·dCTP pair and high misincorporation frequencies for dATP and dGTP with both adducts (compared to dCTP). Collectively, the results indicate that both of these adducts have considerable miscoding potential with some of these polymerases, that there are a number of differences between the 1,N2-ε-Gua and HO-ethanoGua adducts (which formally differ only in the presence of the elements of water), and that misincorporation of dNTPs at a single modified base can vary considerably among different polymerases even in the absence of exonuclease activity.</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>États-Unis</li></country><region><li>Basse-Saxe</li><li>Tennessee</li></region><settlement><li>Göttingen</li></settlement><orgName><li>Université de Göttingen</li></orgName></list><tree><country name="États-Unis"><region name="Tennessee"><name sortKey="Langouet, Sophie" sort="Langouet, Sophie" uniqKey="Langouet S" first="Sophie" last="Langouët">Sophie Langouët</name></region><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name></country><country name="Allemagne"><region name="Basse-Saxe"><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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