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Efficient conversion of N6-threonylcarbamoyladenosine (t6A) into a tRNA native hydantoin cyclic form (ct6A) performed at nucleoside and oligoribonucleotide levels.

Identifieur interne : 000C42 ( PubMed/Curation ); précédent : 000C41; suivant : 000C43

Efficient conversion of N6-threonylcarbamoyladenosine (t6A) into a tRNA native hydantoin cyclic form (ct6A) performed at nucleoside and oligoribonucleotide levels.

Auteurs : Michal Matuszewski [Pologne] ; Katarzyna Debiec ; Elzbieta Sochacka

Source :

RBID : pubmed:28657616

Descripteurs français

English descriptors

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

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pubmed:28657616

Le document en format XML

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<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 wicri:level="1">
<nlm:affiliation>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. elzbieta.sochacka@p.lodz.pl.</nlm:affiliation>
<country xml:lang="fr">Pologne</country>
<wicri:regionArea>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz</wicri:regionArea>
</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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<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 wicri:level="1">
<nlm:affiliation>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. elzbieta.sochacka@p.lodz.pl.</nlm:affiliation>
<country xml:lang="fr">Pologne</country>
<wicri:regionArea>Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz</wicri:regionArea>
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</author>
<author>
<name sortKey="Debiec, Katarzyna" sort="Debiec, Katarzyna" uniqKey="Debiec K" first="Katarzyna" last="Debiec">Katarzyna Debiec</name>
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<author>
<name sortKey="Sochacka, Elzbieta" sort="Sochacka, Elzbieta" uniqKey="Sochacka E" first="Elzbieta" last="Sochacka">Elzbieta Sochacka</name>
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<series>
<title level="j">Chemical communications (Cambridge, England)</title>
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<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="KwdFr" xml:lang="fr">
<term>ARN de transfert de la lysine ()</term>
<term>ARN de transfert de la lysine (synthèse chimique)</term>
<term>Adénosine ()</term>
<term>Adénosine (analogues et dérivés)</term>
<term>Anticodon</term>
<term>Carbodiimides ()</term>
<term>Concentration en ions d'hydrogène</term>
<term>Cyclisation</term>
<term>Escherichia coli</term>
<term>Hydantoïnes ()</term>
<term>Hydantoïnes (synthèse chimique)</term>
<term>Oligoribonucléotides ()</term>
<term>Oligoribonucléotides (synthèse chimique)</term>
<term>Schizosaccharomyces</term>
<term>Stabilité de l'ARN</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" qualifier="analogues et dérivés" xml:lang="fr">
<term>Adénosine</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr">
<term>ARN de transfert de la lysine</term>
<term>Hydantoïnes</term>
<term>Oligoribonucléotides</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>
<keywords scheme="MESH" xml:lang="fr">
<term>ARN de transfert de la lysine</term>
<term>Adénosine</term>
<term>Anticodon</term>
<term>Carbodiimides</term>
<term>Concentration en ions d'hydrogène</term>
<term>Cyclisation</term>
<term>Escherichia coli</term>
<term>Hydantoïnes</term>
<term>Oligoribonucléotides</term>
<term>Schizosaccharomyces</term>
<term>Stabilité de l'ARN</term>
</keywords>
</textClass>
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<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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<MedlineTA>Chem Commun (Camb)</MedlineTA>
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<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>
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<RegistryNumber>0</RegistryNumber>
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</Chemical>
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</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>
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<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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<History>
<PubMedPubDate PubStatus="pubmed">
<Year>2017</Year>
<Month>6</Month>
<Day>29</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
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<Month>4</Month>
<Day>28</Day>
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<Minute>0</Minute>
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<ArticleId IdType="doi">10.1039/c7cc03560h</ArticleId>
</ArticleIdList>
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</record>

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