Efficient conversion of N6-threonylcarbamoyladenosine (t6A) into a tRNA native hydantoin cyclic form (ct6A) performed at nucleoside and oligoribonucleotide levels.
Identifieur interne : 000C42 ( PubMed/Corpus ); précédent : 000C41; suivant : 000C43Efficient conversion of N6-threonylcarbamoyladenosine (t6A) into a tRNA native hydantoin cyclic form (ct6A) performed at nucleoside and oligoribonucleotide levels.
Auteurs : Michal Matuszewski ; Katarzyna Debiec ; Elzbieta SochackaSource :
- Chemical communications (Cambridge, England) [ 1364-548X ] ; 2017.
English descriptors
- KwdEn :
- Adenosine (analogs & derivatives), Adenosine (chemistry), Anticodon, Carbodiimides (chemistry), Cyclization, Escherichia coli, Hydantoins (chemical synthesis), Hydantoins (chemistry), Hydrogen-Ion Concentration, Oligoribonucleotides (chemical synthesis), Oligoribonucleotides (chemistry), RNA Stability, RNA, Transfer, Lys (chemical synthesis), RNA, Transfer, Lys (chemistry), Schizosaccharomyces.
- MESH :
- chemical , analogs & derivatives : Adenosine.
- chemical , chemical synthesis : Hydantoins, Oligoribonucleotides, RNA, Transfer, Lys.
- chemical , chemistry : Adenosine, Carbodiimides, Hydantoins, Oligoribonucleotides, RNA, Transfer, Lys.
- chemical : Anticodon.
- Cyclization, Escherichia coli, Hydrogen-Ion Concentration, RNA Stability, Schizosaccharomyces.
Abstract
A t6A nucleoside was efficiently and stereospecifically transformed into a hydantoin cyclic form of N6-l-threonylcarbamoyladenosine (ct6A) by the use of polymer bounded carbodiimide (EDC-P) and HOBt. The procedure was successfully applied for a post-synthetic conversion of t6A-containing RNA 17-mers (of the sequences of anticodon stem and loop (ASL) fragments of S. pombe tRNAi and E. coli tRNALys) into the products bearing the ct6A unit.
DOI: 10.1039/c7cc03560h
PubMed: 28657616
Links to Exploration step
pubmed:28657616Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Efficient conversion of N<sup>6</sup>
-threonylcarbamoyladenosine (t<sup>6</sup>
A) into a tRNA native hydantoin cyclic form (ct<sup>6</sup>
A) performed at nucleoside and oligoribonucleotide levels.</title>
<author><name sortKey="Matuszewski, Michal" sort="Matuszewski, Michal" uniqKey="Matuszewski M" first="Michal" last="Matuszewski">Michal Matuszewski</name>
<affiliation><nlm:affiliation>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. elzbieta.sochacka@p.lodz.pl.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Debiec, Katarzyna" sort="Debiec, Katarzyna" uniqKey="Debiec K" first="Katarzyna" last="Debiec">Katarzyna Debiec</name>
</author>
<author><name sortKey="Sochacka, Elzbieta" sort="Sochacka, Elzbieta" uniqKey="Sochacka E" first="Elzbieta" last="Sochacka">Elzbieta Sochacka</name>
</author>
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<idno type="doi">10.1039/c7cc03560h</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Efficient conversion of N<sup>6</sup>
-threonylcarbamoyladenosine (t<sup>6</sup>
A) into a tRNA native hydantoin cyclic form (ct<sup>6</sup>
A) performed at nucleoside and oligoribonucleotide levels.</title>
<author><name sortKey="Matuszewski, Michal" sort="Matuszewski, Michal" uniqKey="Matuszewski M" first="Michal" last="Matuszewski">Michal Matuszewski</name>
<affiliation><nlm:affiliation>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. elzbieta.sochacka@p.lodz.pl.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Debiec, Katarzyna" sort="Debiec, Katarzyna" uniqKey="Debiec K" first="Katarzyna" last="Debiec">Katarzyna Debiec</name>
</author>
<author><name sortKey="Sochacka, Elzbieta" sort="Sochacka, Elzbieta" uniqKey="Sochacka E" first="Elzbieta" last="Sochacka">Elzbieta Sochacka</name>
</author>
</analytic>
<series><title level="j">Chemical communications (Cambridge, England)</title>
<idno type="eISSN">1364-548X</idno>
<imprint><date when="2017" type="published">2017</date>
</imprint>
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</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Adenosine (analogs & derivatives)</term>
<term>Adenosine (chemistry)</term>
<term>Anticodon</term>
<term>Carbodiimides (chemistry)</term>
<term>Cyclization</term>
<term>Escherichia coli</term>
<term>Hydantoins (chemical synthesis)</term>
<term>Hydantoins (chemistry)</term>
<term>Hydrogen-Ion Concentration</term>
<term>Oligoribonucleotides (chemical synthesis)</term>
<term>Oligoribonucleotides (chemistry)</term>
<term>RNA Stability</term>
<term>RNA, Transfer, Lys (chemical synthesis)</term>
<term>RNA, Transfer, Lys (chemistry)</term>
<term>Schizosaccharomyces</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Adenosine</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Hydantoins</term>
<term>Oligoribonucleotides</term>
<term>RNA, Transfer, Lys</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Adenosine</term>
<term>Carbodiimides</term>
<term>Hydantoins</term>
<term>Oligoribonucleotides</term>
<term>RNA, Transfer, Lys</term>
</keywords>
<keywords scheme="MESH" type="chemical" xml:lang="en"><term>Anticodon</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Cyclization</term>
<term>Escherichia coli</term>
<term>Hydrogen-Ion Concentration</term>
<term>RNA Stability</term>
<term>Schizosaccharomyces</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A t<sup>6</sup>
A nucleoside was efficiently and stereospecifically transformed into a hydantoin cyclic form of N<sup>6</sup>
-l-threonylcarbamoyladenosine (ct<sup>6</sup>
A) by the use of polymer bounded carbodiimide (EDC-P) and HOBt. The procedure was successfully applied for a post-synthetic conversion of t<sup>6</sup>
A-containing RNA 17-mers (of the sequences of anticodon stem and loop (ASL) fragments of S. pombe tRNA<sup>i</sup>
and E. coli tRNA<sup>Lys</sup>
) into the products bearing the ct<sup>6</sup>
A unit.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28657616</PMID>
<DateCompleted><Year>2018</Year>
<Month>04</Month>
<Day>27</Day>
</DateCompleted>
<DateRevised><Year>2018</Year>
<Month>04</Month>
<Day>27</Day>
</DateRevised>
<Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1364-548X</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>53</Volume>
<Issue>56</Issue>
<PubDate><Year>2017</Year>
<Month>Jul</Month>
<Day>11</Day>
</PubDate>
</JournalIssue>
<Title>Chemical communications (Cambridge, England)</Title>
<ISOAbbreviation>Chem. Commun. (Camb.)</ISOAbbreviation>
</Journal>
<ArticleTitle>Efficient conversion of N<sup>6</sup>
-threonylcarbamoyladenosine (t<sup>6</sup>
A) into a tRNA native hydantoin cyclic form (ct<sup>6</sup>
A) performed at nucleoside and oligoribonucleotide levels.</ArticleTitle>
<Pagination><MedlinePgn>7945-7948</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1039/c7cc03560h</ELocationID>
<Abstract><AbstractText>A t<sup>6</sup>
A nucleoside was efficiently and stereospecifically transformed into a hydantoin cyclic form of N<sup>6</sup>
-l-threonylcarbamoyladenosine (ct<sup>6</sup>
A) by the use of polymer bounded carbodiimide (EDC-P) and HOBt. The procedure was successfully applied for a post-synthetic conversion of t<sup>6</sup>
A-containing RNA 17-mers (of the sequences of anticodon stem and loop (ASL) fragments of S. pombe tRNA<sup>i</sup>
and E. coli tRNA<sup>Lys</sup>
) into the products bearing the ct<sup>6</sup>
A unit.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Matuszewski</LastName>
<ForeName>Michal</ForeName>
<Initials>M</Initials>
<AffiliationInfo><Affiliation>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. elzbieta.sochacka@p.lodz.pl.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Debiec</LastName>
<ForeName>Katarzyna</ForeName>
<Initials>K</Initials>
</Author>
<Author ValidYN="Y"><LastName>Sochacka</LastName>
<ForeName>Elzbieta</ForeName>
<Initials>E</Initials>
</Author>
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<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
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<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Chem Commun (Camb)</MedlineTA>
<NlmUniqueID>9610838</NlmUniqueID>
<ISSNLinking>1359-7345</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000926">Anticodon</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D002234">Carbodiimides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D006827">Hydantoins</NameOfSubstance>
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<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D009843">Oligoribonucleotides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D012357">RNA, Transfer, Lys</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>24719-82-2</RegistryNumber>
<NameOfSubstance UI="C003268">N(6)-(N-threonylcarbonyl)adenosine</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>K72T3FS567</RegistryNumber>
<NameOfSubstance UI="D000241">Adenosine</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000241" MajorTopicYN="N">Adenosine</DescriptorName>
<QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000926" MajorTopicYN="N">Anticodon</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D002234" MajorTopicYN="N">Carbodiimides</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D003500" MajorTopicYN="N">Cyclization</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004926" MajorTopicYN="N">Escherichia coli</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006827" MajorTopicYN="N">Hydantoins</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006863" MajorTopicYN="N">Hydrogen-Ion Concentration</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009843" MajorTopicYN="N">Oligoribonucleotides</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D020871" MajorTopicYN="N">RNA Stability</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D012357" MajorTopicYN="N">RNA, Transfer, Lys</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D012568" MajorTopicYN="N">Schizosaccharomyces</DescriptorName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
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