Chemical consequences of incorporation of 5-fluorouracil into DNA as studied by NMR.
Identifieur interne : 002A77 ( PubMed/Corpus ); précédent : 002A76; suivant : 002A78Chemical consequences of incorporation of 5-fluorouracil into DNA as studied by NMR.
Auteurs : A B Kremer ; T. Mikita ; G P BeardsleySource :
- Biochemistry [ 0006-2960 ] ; 1987.
English descriptors
- KwdEn :
- MESH :
- chemical , biosynthesis : DNA.
- chemical , chemical synthesis : Oligodeoxyribonucleotides.
- chemical , metabolism : Fluorouracil.
- Base Composition, Base Sequence, Magnetic Resonance Spectroscopy, Nucleic Acid Conformation.
Abstract
The cytotoxic analogue of thymine, 5-fluorouracil (Uf), is known to be incorporated into DNA in biological systems. This abnormal base has been synthetically incorporated into short DNA oligomers. The ionization of the N-3 proton of this base within DNA oligomers was measured by observation of the 19F chemical shift at varying pH values. The pKa values for the Uf ring of dTpdUfpdT and dApdUfpdA were determined to be 7.84 and 7.9, respectively. The self-complementary 12-mers d(G-C-G-C-A-A-T-Uf-G-C-G-C) and d(C-G-A-T-Uf-A-T-A-A-T-C-G) were synthesized, and 1H NMR was used to compare the helix dynamics and stability of the interstrand imino proton hydrogen bonds with those of the 12-mers d(G-C-G-C-A-A-T-T-G-C-G-C) and d(C-G-A-T-T-A-T-A-A-T-C-G). The N-3 hydrogen bond of the A-Uf base pair was less stable than the corresponding hydrogen bond in A-T base pairs in the same helix, and the A-Uf base pair was less stable than the A-T base pair in the analogous position of the control helix. The observed temperature-dependent dynamics and NMR melting temperatures of the control and dUf-containing oligomers were similar.
DOI: 10.1021/bi00376a009
PubMed: 3828314
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pubmed:3828314Le document en format XML
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Mikita</name></author><author><name sortKey="Beardsley, G P" sort="Beardsley, G P" uniqKey="Beardsley G" first="G P" last="Beardsley">G P Beardsley</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1987">1987</date><idno type="RBID">pubmed:3828314</idno><idno type="pmid">3828314</idno><idno type="doi">10.1021/bi00376a009</idno><idno type="wicri:Area/PubMed/Corpus">002A77</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002A77</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Chemical consequences of incorporation of 5-fluorouracil into DNA as studied by NMR.</title><author><name sortKey="Kremer, A B" sort="Kremer, A B" uniqKey="Kremer A" first="A B" last="Kremer">A B Kremer</name></author><author><name sortKey="Mikita, T" sort="Mikita, T" uniqKey="Mikita T" first="T" last="Mikita">T. Mikita</name></author><author><name sortKey="Beardsley, G P" sort="Beardsley, G P" uniqKey="Beardsley G" first="G P" last="Beardsley">G P Beardsley</name></author></analytic><series><title level="j">Biochemistry</title><idno type="ISSN">0006-2960</idno><imprint><date when="1987" type="published">1987</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Composition</term><term>Base Sequence</term><term>DNA (biosynthesis)</term><term>Fluorouracil (metabolism)</term><term>Magnetic Resonance Spectroscopy</term><term>Nucleic Acid Conformation</term><term>Oligodeoxyribonucleotides (chemical synthesis)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>DNA</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Fluorouracil</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Composition</term><term>Base Sequence</term><term>Magnetic Resonance Spectroscopy</term><term>Nucleic Acid Conformation</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The cytotoxic analogue of thymine, 5-fluorouracil (Uf), is known to be incorporated into DNA in biological systems. This abnormal base has been synthetically incorporated into short DNA oligomers. The ionization of the N-3 proton of this base within DNA oligomers was measured by observation of the 19F chemical shift at varying pH values. The pKa values for the Uf ring of dTpdUfpdT and dApdUfpdA were determined to be 7.84 and 7.9, respectively. The self-complementary 12-mers d(G-C-G-C-A-A-T-Uf-G-C-G-C) and d(C-G-A-T-Uf-A-T-A-A-T-C-G) were synthesized, and 1H NMR was used to compare the helix dynamics and stability of the interstrand imino proton hydrogen bonds with those of the 12-mers d(G-C-G-C-A-A-T-T-G-C-G-C) and d(C-G-A-T-T-A-T-A-A-T-C-G). The N-3 hydrogen bond of the A-Uf base pair was less stable than the corresponding hydrogen bond in A-T base pairs in the same helix, and the A-Uf base pair was less stable than the A-T base pair in the analogous position of the control helix. The observed temperature-dependent dynamics and NMR melting temperatures of the control and dUf-containing oligomers were similar.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">3828314</PMID><DateCompleted><Year>1987</Year><Month>05</Month><Day>20</Day></DateCompleted><DateRevised><Year>2019</Year><Month>06</Month><Day>13</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0006-2960</ISSN><JournalIssue CitedMedium="Print"><Volume>26</Volume><Issue>2</Issue><PubDate><Year>1987</Year><Month>Jan</Month><Day>27</Day></PubDate></JournalIssue><Title>Biochemistry</Title><ISOAbbreviation>Biochemistry</ISOAbbreviation></Journal><ArticleTitle>Chemical consequences of incorporation of 5-fluorouracil into DNA as studied by NMR.</ArticleTitle><Pagination><MedlinePgn>391-7</MedlinePgn></Pagination><Abstract><AbstractText>The cytotoxic analogue of thymine, 5-fluorouracil (Uf), is known to be incorporated into DNA in biological systems. This abnormal base has been synthetically incorporated into short DNA oligomers. The ionization of the N-3 proton of this base within DNA oligomers was measured by observation of the 19F chemical shift at varying pH values. The pKa values for the Uf ring of dTpdUfpdT and dApdUfpdA were determined to be 7.84 and 7.9, respectively. The self-complementary 12-mers d(G-C-G-C-A-A-T-Uf-G-C-G-C) and d(C-G-A-T-Uf-A-T-A-A-T-C-G) were synthesized, and 1H NMR was used to compare the helix dynamics and stability of the interstrand imino proton hydrogen bonds with those of the 12-mers d(G-C-G-C-A-A-T-T-G-C-G-C) and d(C-G-A-T-T-A-T-A-A-T-C-G). The N-3 hydrogen bond of the A-Uf base pair was less stable than the corresponding hydrogen bond in A-T base pairs in the same helix, and the A-Uf base pair was less stable than the A-T base pair in the analogous position of the control helix. The observed temperature-dependent dynamics and NMR melting temperatures of the control and dUf-containing oligomers were similar.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kremer</LastName><ForeName>A B</ForeName><Initials>AB</Initials></Author><Author ValidYN="Y"><LastName>Mikita</LastName><ForeName>T</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Beardsley</LastName><ForeName>G P</ForeName><Initials>GP</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>R0-1 CA 42300</GrantID><Acronym>CA</Acronym><Agency>NCI NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013487">Research Support, U.S. Gov't, P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Biochemistry</MedlineTA><NlmUniqueID>0370623</NlmUniqueID><ISSNLinking>0006-2960</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009838">Oligodeoxyribonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>U3P01618RT</RegistryNumber><NameOfSubstance UI="D005472">Fluorouracil</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001482" MajorTopicYN="N">Base Composition</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000096" MajorTopicYN="Y">biosynthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005472" MajorTopicYN="Y">Fluorouracil</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009682" MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009690" MajorTopicYN="N">Nucleic Acid Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009838" MajorTopicYN="N">Oligodeoxyribonucleotides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1987</Year><Month>1</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>1987</Year><Month>1</Month><Day>27</Day><Hour>0</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1987</Year><Month>1</Month><Day>27</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">3828314</ArticleId><ArticleId IdType="doi">10.1021/bi00376a009</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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