Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.
Identifieur interne : 002A68 ( PubMed/Curation ); précédent : 002A67; suivant : 002A69Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.
Auteurs : J C Schulhof [France] ; D. Molko ; R. TeouleSource :
- Nucleic acids research [ 0305-1048 ] ; 1988.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Thymine.
- synthèse chimique : ADN, Oligodésoxyribonucléotides.
- Indicateurs et réactifs, Spectrométrie de masse.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Thymine.
- chemical , chemical synthesis : DNA, Oligodeoxyribonucleotides.
- chemical : Indicators and Reagents.
- Mass Spectrometry.
Abstract
5,6-Dihydrothymine is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions. This modified base is unstable in the deprotection conditions used for classical synthesis of oligonucleotides. For its incorporation in synthetic DNA fragments, a new set of amino protecting groups has been developed. The 5,6-dihydrothymidine phosphoramidite was successfully employed for the synthesis of two 14-mers and one 17-mer bearing this defect at positions corresponding to restriction enzymes sites. The presence of the modified base still intact in the oligonucleotides was evidenced by mass spectrometry in pyrolytic conditions.
DOI: 10.1093/nar/16.1.319
PubMed: 3340528
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Molko</name></author><author><name sortKey="Teoule, R" sort="Teoule, R" uniqKey="Teoule R" first="R" last="Teoule">R. Teoule</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1988" type="published">1988</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>DNA (chemical synthesis)</term><term>Indicators and Reagents</term><term>Mass Spectrometry</term><term>Oligodeoxyribonucleotides (chemical synthesis)</term><term>Thymine (analogs & derivatives)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN (synthèse chimique)</term><term>Indicateurs et réactifs</term><term>Oligodésoxyribonucléotides (synthèse chimique)</term><term>Spectrométrie de masse</term><term>Thymine (analogues et dérivés)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Thymine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>DNA</term><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Indicators and Reagents</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Thymine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>ADN</term><term>Oligodésoxyribonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Mass Spectrometry</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Indicateurs et réactifs</term><term>Spectrométrie de masse</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">5,6-Dihydrothymine is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions. This modified base is unstable in the deprotection conditions used for classical synthesis of oligonucleotides. For its incorporation in synthetic DNA fragments, a new set of amino protecting groups has been developed. The 5,6-dihydrothymidine phosphoramidite was successfully employed for the synthesis of two 14-mers and one 17-mer bearing this defect at positions corresponding to restriction enzymes sites. The presence of the modified base still intact in the oligonucleotides was evidenced by mass spectrometry in pyrolytic conditions.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">3340528</PMID><DateCompleted><Year>1988</Year><Month>03</Month><Day>07</Day></DateCompleted><DateRevised><Year>2019</Year><Month>05</Month><Day>01</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0305-1048</ISSN><JournalIssue CitedMedium="Print"><Volume>16</Volume><Issue>1</Issue><PubDate><Year>1988</Year><Month>Jan</Month><Day>11</Day></PubDate></JournalIssue><Title>Nucleic acids research</Title><ISOAbbreviation>Nucleic Acids Res.</ISOAbbreviation></Journal><ArticleTitle>Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.</ArticleTitle><Pagination><MedlinePgn>319-26</MedlinePgn></Pagination><Abstract><AbstractText>5,6-Dihydrothymine is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions. This modified base is unstable in the deprotection conditions used for classical synthesis of oligonucleotides. For its incorporation in synthetic DNA fragments, a new set of amino protecting groups has been developed. The 5,6-dihydrothymidine phosphoramidite was successfully employed for the synthesis of two 14-mers and one 17-mer bearing this defect at positions corresponding to restriction enzymes sites. The presence of the modified base still intact in the oligonucleotides was evidenced by mass spectrometry in pyrolytic conditions.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Schulhof</LastName><ForeName>J C</ForeName><Initials>JC</Initials><AffiliationInfo><Affiliation>Département de Recherche Fondamentale de Grenoble, Centre d'Etudes, Nucléaires de Grenoble, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Molko</LastName><ForeName>D</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Teoule</LastName><ForeName>R</ForeName><Initials>R</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Nucleic Acids 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