Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of chemically modified oligonucleotides.
Identifieur interne : 002956 ( Ncbi/Merge ); précédent : 002955; suivant : 002957Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of chemically modified oligonucleotides.
Auteurs : B H Wang ; K. BiemannSource :
- Analytical chemistry [ 0003-2700 ] ; 1994.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , analysis : Oligodeoxyribonucleotides, Oligoribonucleotides.
- chemical , chemistry : Oligodeoxyribonucleotides, Oligoribonucleotides.
- methods : Mass Spectrometry.
- Base Sequence, Calibration, Molecular Sequence Data, Molecular Weight.
Abstract
A variety of chemically modified oligonucleotides have been studied by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) in the negative ion mode. These include oligonucleotides containing modified bases, such as uracil glycol, bromoguanine, O6-butylguanine, as well as oligonucleotides in which the phosphodiester groups had been replaced by other functional groups, such as phosphorothioates. With the linear TOF mass spectrometer, there is no or very little fragmentation observed, and the determination of the molecular weight by MALDI-TOFMS offers a convenient way for identifying/confirming the presence of the modification. With internal calibration, a mass accuracy of 0.01% can be achieved. Such mass accuracy makes it possible to directly differentiate a small uridine-containing oligonucleotide from its cytidine-containing analogue. Because of factors such as sample inhomogeneity, laser output fluctuation, and the dynamic range of the detector, quantitation by MALDI-TOFMS has been difficult. Nevertheless, semiquantitative information can be obtained for those analytes that are closely related in structure. Monitoring the products of the synthesis of monophosphorothioated oligoribonucleotide 16-mers by MALDI-TOFMS revealed that the sulfur atom in the phosphorothioate group can be replaced by an oxygen atom during the succeeding introduction of phosphodiester groups. The earlier the phosphorothioate group is introduced during the synthesis of the 16-mer, the greater is the extent of sulfur to oxygen replacement.
DOI: 10.1021/ac00083a023
PubMed: 8030793
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of chemically modified oligonucleotides.</title><author><name sortKey="Wang, B H" sort="Wang, B H" uniqKey="Wang B" first="B H" last="Wang">B H Wang</name><affiliation><nlm:affiliation>Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139-4307.</nlm:affiliation><wicri:noCountry code="subField">Cambridge 02139-4307</wicri:noCountry></affiliation></author><author><name sortKey="Biemann, K" sort="Biemann, K" uniqKey="Biemann K" first="K" last="Biemann">K. Biemann</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1994">1994</date><idno type="RBID">pubmed:8030793</idno><idno type="pmid">8030793</idno><idno type="doi">10.1021/ac00083a023</idno><idno type="wicri:Area/PubMed/Corpus">002877</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002877</idno><idno type="wicri:Area/PubMed/Curation">002877</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002877</idno><idno type="wicri:Area/PubMed/Checkpoint">002725</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">002725</idno><idno type="wicri:Area/Ncbi/Merge">002956</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of chemically modified oligonucleotides.</title><author><name sortKey="Wang, B H" sort="Wang, B H" uniqKey="Wang B" first="B H" last="Wang">B H Wang</name><affiliation><nlm:affiliation>Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139-4307.</nlm:affiliation><wicri:noCountry code="subField">Cambridge 02139-4307</wicri:noCountry></affiliation></author><author><name sortKey="Biemann, K" sort="Biemann, K" uniqKey="Biemann K" first="K" last="Biemann">K. Biemann</name></author></analytic><series><title level="j">Analytical chemistry</title><idno type="ISSN">0003-2700</idno><imprint><date when="1994" type="published">1994</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Sequence</term><term>Calibration</term><term>Mass Spectrometry (methods)</term><term>Molecular Sequence Data</term><term>Molecular Weight</term><term>Oligodeoxyribonucleotides (analysis)</term><term>Oligodeoxyribonucleotides (chemistry)</term><term>Oligoribonucleotides (analysis)</term><term>Oligoribonucleotides (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Calibrage</term><term>Données de séquences moléculaires</term><term>Masse moléculaire</term><term>Oligodésoxyribonucléotides ()</term><term>Oligodésoxyribonucléotides (analyse)</term><term>Oligoribonucléotides ()</term><term>Oligoribonucléotides (analyse)</term><term>Spectrométrie de masse ()</term><term>Séquence nucléotidique</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Oligodeoxyribonucleotides</term><term>Oligoribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Oligodeoxyribonucleotides</term><term>Oligoribonucleotides</term></keywords><keywords scheme="MESH" qualifier="analyse" xml:lang="fr"><term>Oligodésoxyribonucléotides</term><term>Oligoribonucléotides</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Mass Spectrometry</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Calibration</term><term>Molecular Sequence Data</term><term>Molecular Weight</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Calibrage</term><term>Données de séquences moléculaires</term><term>Masse moléculaire</term><term>Oligodésoxyribonucléotides</term><term>Oligoribonucléotides</term><term>Spectrométrie de masse</term><term>Séquence nucléotidique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A variety of chemically modified oligonucleotides have been studied by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) in the negative ion mode. These include oligonucleotides containing modified bases, such as uracil glycol, bromoguanine, O6-butylguanine, as well as oligonucleotides in which the phosphodiester groups had been replaced by other functional groups, such as phosphorothioates. With the linear TOF mass spectrometer, there is no or very little fragmentation observed, and the determination of the molecular weight by MALDI-TOFMS offers a convenient way for identifying/confirming the presence of the modification. With internal calibration, a mass accuracy of 0.01% can be achieved. Such mass accuracy makes it possible to directly differentiate a small uridine-containing oligonucleotide from its cytidine-containing analogue. Because of factors such as sample inhomogeneity, laser output fluctuation, and the dynamic range of the detector, quantitation by MALDI-TOFMS has been difficult. Nevertheless, semiquantitative information can be obtained for those analytes that are closely related in structure. Monitoring the products of the synthesis of monophosphorothioated oligoribonucleotide 16-mers by MALDI-TOFMS revealed that the sulfur atom in the phosphorothioate group can be replaced by an oxygen atom during the succeeding introduction of phosphodiester groups. The earlier the phosphorothioate group is introduced during the synthesis of the 16-mer, the greater is the extent of sulfur to oxygen replacement.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">8030793</PMID><DateCompleted><Year>1994</Year><Month>08</Month><Day>08</Day></DateCompleted><DateRevised><Year>2019</Year><Month>07</Month><Day>17</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0003-2700</ISSN><JournalIssue CitedMedium="Print"><Volume>66</Volume><Issue>11</Issue><PubDate><Year>1994</Year><Month>Jun</Month><Day>01</Day></PubDate></JournalIssue><Title>Analytical chemistry</Title><ISOAbbreviation>Anal. Chem.</ISOAbbreviation></Journal><ArticleTitle>Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of chemically modified oligonucleotides.</ArticleTitle><Pagination><MedlinePgn>1918-24</MedlinePgn></Pagination><Abstract><AbstractText>A variety of chemically modified oligonucleotides have been studied by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) in the negative ion mode. These include oligonucleotides containing modified bases, such as uracil glycol, bromoguanine, O6-butylguanine, as well as oligonucleotides in which the phosphodiester groups had been replaced by other functional groups, such as phosphorothioates. With the linear TOF mass spectrometer, there is no or very little fragmentation observed, and the determination of the molecular weight by MALDI-TOFMS offers a convenient way for identifying/confirming the presence of the modification. With internal calibration, a mass accuracy of 0.01% can be achieved. Such mass accuracy makes it possible to directly differentiate a small uridine-containing oligonucleotide from its cytidine-containing analogue. Because of factors such as sample inhomogeneity, laser output fluctuation, and the dynamic range of the detector, quantitation by MALDI-TOFMS has been difficult. Nevertheless, semiquantitative information can be obtained for those analytes that are closely related in structure. Monitoring the products of the synthesis of monophosphorothioated oligoribonucleotide 16-mers by MALDI-TOFMS revealed that the sulfur atom in the phosphorothioate group can be replaced by an oxygen atom during the succeeding introduction of phosphodiester groups. The earlier the phosphorothioate group is introduced during the synthesis of the 16-mer, the greater is the extent of sulfur to oxygen replacement.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>B H</ForeName><Initials>BH</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139-4307.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Biemann</LastName><ForeName>K</ForeName><Initials>K</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>NCRR RR-00317</GrantID><Acronym>RR</Acronym><Agency>NCRR 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>Anal Chem</MedlineTA><NlmUniqueID>0370536</NlmUniqueID><ISSNLinking>0003-2700</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009838">Oligodeoxyribonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009843">Oligoribonucleotides</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002138" MajorTopicYN="N">Calibration</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013058" MajorTopicYN="N">Mass Spectrometry</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008969" MajorTopicYN="N">Molecular Sequence Data</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008970" MajorTopicYN="N">Molecular Weight</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009838" MajorTopicYN="N">Oligodeoxyribonucleotides</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="Y">analysis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009843" MajorTopicYN="N">Oligoribonucleotides</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="Y">analysis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1994</Year><Month>6</Month><Day>1</Day></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>1994</Year><Month>6</Month><Day>1</Day><Hour>0</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1994</Year><Month>6</Month><Day>1</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">8030793</ArticleId><ArticleId IdType="doi">10.1021/ac00083a023</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list></list><tree><noCountry><name sortKey="Biemann, K" sort="Biemann, K" uniqKey="Biemann K" first="K" last="Biemann">K. Biemann</name><name sortKey="Wang, B H" sort="Wang, B H" uniqKey="Wang B" first="B H" last="Wang">B H Wang</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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