Chemical synthesis of the 5-taurinomethyl(-2-thio)uridine modified anticodon arm of the human mitochondrial tRNA(Leu(UUR)) and tRNA(Lys).
Identifieur interne : 001971 ( PubMed/Checkpoint ); précédent : 001970; suivant : 001972Chemical synthesis of the 5-taurinomethyl(-2-thio)uridine modified anticodon arm of the human mitochondrial tRNA(Leu(UUR)) and tRNA(Lys).
Auteurs : Grazyna Leszczynska [Pologne] ; Piotr Leonczak [Pologne] ; Karolina Wozniak [Pologne] ; Andrzej Malkiewicz [Pologne]Source :
- RNA (New York, N.Y.) [ 1469-9001 ] ; 2014.
Descripteurs français
- KwdFr :
- 4-Thiouridine (analogues et dérivés), 4-Thiouridine (synthèse chimique), ARN de transfert de la leucine (génétique), ARN de transfert de la lysine (génétique), Anticodon (génétique), Conformation d'acide nucléique, Humains, Mitochondries (génétique), Mutation (génétique), Oligoribonucléotides (génétique).
- MESH :
- analogues et dérivés : 4-Thiouridine.
- génétique : ARN de transfert de la leucine, ARN de transfert de la lysine, Anticodon, Mitochondries, Mutation, Oligoribonucléotides.
- synthèse chimique : 4-Thiouridine.
- Conformation d'acide nucléique, Humains.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Thiouridine.
- chemical , chemical synthesis : Thiouridine.
- chemical , genetics : Anticodon, Oligoribonucleotides, RNA, Transfer, Leu, RNA, Transfer, Lys.
- genetics : Mitochondria, Mutation.
- Humans, Nucleic Acid Conformation.
Abstract
5-Taurinomethyluridine (τm(5)U) and 5-taurinomethyl-2-thiouridine (τm(5)s(2)U) are located at the wobble position of human mitochondrial (hmt) tRNA(Leu(UUR)) and tRNA(Lys), respectively. Both hypermodified units restrict decoding of the third codon letter to A and G. Pathogenic mutations in the genes encoding hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys) are responsible for the loss of the discussed modifications and, as a consequence, for the occurrence of severe mitochondrial dysfunctions (MELAS, MERRF). Synthetic oligoribonucleotides bearing modified nucleosides are a versatile tool for studying mechanisms of genetic message translation and accompanying pathologies at nucleoside resolution. In this paper, we present site-specific chemical incorporation of τm(5)U and τm(5)s(2)U into 17-mers related to the sequence of the anticodon arms hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys), respectively employing phosphoramidite chemistry on CPG support. Selected protecting groups for the sulfonic acid (4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutyl) and the exoamine function (-C(O)CF3) are compatible with the blockage of the canonical monomeric units. The synthesis of τm(5)s(2)U-modified RNA fragment was performed under conditions eliminating the formation of side products of 2-thiocarbonyl group oxidation and/or oxidative desulphurization. The structure of the final oligomers was confirmed by mass spectroscopy and enzymatic cleavage data.
DOI: 10.1261/rna.044412.114
PubMed: 24757169
Affiliations:
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Poland.</nlm:affiliation><country xml:lang="fr">Pologne</country><wicri:regionArea>Institute of Organic Chemistry, Lodz University of Technology, 90-924 Lodz</wicri:regionArea><wicri:noRegion>90-924 Lodz</wicri:noRegion></affiliation></author></analytic><series><title level="j">RNA (New York, N.Y.)</title><idno type="eISSN">1469-9001</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anticodon (genetics)</term><term>Humans</term><term>Mitochondria (genetics)</term><term>Mutation (genetics)</term><term>Nucleic Acid Conformation</term><term>Oligoribonucleotides (genetics)</term><term>RNA, Transfer, Leu (genetics)</term><term>RNA, Transfer, Lys (genetics)</term><term>Thiouridine (analogs & derivatives)</term><term>Thiouridine (chemical synthesis)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>4-Thiouridine (analogues et 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xml:lang="en"><term>Mitochondria</term><term>Mutation</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>ARN de transfert de la leucine</term><term>ARN de transfert de la lysine</term><term>Anticodon</term><term>Mitochondries</term><term>Mutation</term><term>Oligoribonucléotides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>4-Thiouridine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Humans</term><term>Nucleic Acid Conformation</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Conformation d'acide nucléique</term><term>Humains</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">5-Taurinomethyluridine (τm(5)U) and 5-taurinomethyl-2-thiouridine (τm(5)s(2)U) are located at the wobble position of human mitochondrial (hmt) tRNA(Leu(UUR)) and tRNA(Lys), respectively. Both hypermodified units restrict decoding of the third codon letter to A and G. Pathogenic mutations in the genes encoding hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys) are responsible for the loss of the discussed modifications and, as a consequence, for the occurrence of severe mitochondrial dysfunctions (MELAS, MERRF). Synthetic oligoribonucleotides bearing modified nucleosides are a versatile tool for studying mechanisms of genetic message translation and accompanying pathologies at nucleoside resolution. In this paper, we present site-specific chemical incorporation of τm(5)U and τm(5)s(2)U into 17-mers related to the sequence of the anticodon arms hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys), respectively employing phosphoramidite chemistry on CPG support. Selected protecting groups for the sulfonic acid (4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutyl) and the exoamine function (-C(O)CF3) are compatible with the blockage of the canonical monomeric units. The synthesis of τm(5)s(2)U-modified RNA fragment was performed under conditions eliminating the formation of side products of 2-thiocarbonyl group oxidation and/or oxidative desulphurization. The structure of the final oligomers was confirmed by mass spectroscopy and enzymatic cleavage data. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">24757169</PMID><DateCompleted><Year>2014</Year><Month>07</Month><Day>11</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1469-9001</ISSN><JournalIssue CitedMedium="Internet"><Volume>20</Volume><Issue>6</Issue><PubDate><Year>2014</Year><Month>Jun</Month></PubDate></JournalIssue><Title>RNA (New York, N.Y.)</Title><ISOAbbreviation>RNA</ISOAbbreviation></Journal><ArticleTitle>Chemical synthesis of the 5-taurinomethyl(-2-thio)uridine modified anticodon arm of the human mitochondrial tRNA(Leu(UUR)) and tRNA(Lys).</ArticleTitle><Pagination><MedlinePgn>938-47</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1261/rna.044412.114</ELocationID><Abstract><AbstractText>5-Taurinomethyluridine (τm(5)U) and 5-taurinomethyl-2-thiouridine (τm(5)s(2)U) are located at the wobble position of human mitochondrial (hmt) tRNA(Leu(UUR)) and tRNA(Lys), respectively. Both hypermodified units restrict decoding of the third codon letter to A and G. Pathogenic mutations in the genes encoding hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys) are responsible for the loss of the discussed modifications and, as a consequence, for the occurrence of severe mitochondrial dysfunctions (MELAS, MERRF). Synthetic oligoribonucleotides bearing modified nucleosides are a versatile tool for studying mechanisms of genetic message translation and accompanying pathologies at nucleoside resolution. In this paper, we present site-specific chemical incorporation of τm(5)U and τm(5)s(2)U into 17-mers related to the sequence of the anticodon arms hmt-tRNA(Leu(UUR)) and hmt-tRNA(Lys), respectively employing phosphoramidite chemistry on CPG support. Selected protecting groups for the sulfonic acid (4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutyl) and the exoamine function (-C(O)CF3) are compatible with the blockage of the canonical monomeric units. The synthesis of τm(5)s(2)U-modified RNA fragment was performed under conditions eliminating the formation of side products of 2-thiocarbonyl group oxidation and/or oxidative desulphurization. The structure of the final oligomers was confirmed by mass spectroscopy and enzymatic cleavage data. </AbstractText><CopyrightInformation>© 2014 Leszczynska et al.; Published by Cold Spring Harbor Laboratory Press for the RNA Society.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Leszczynska</LastName><ForeName>Grazyna</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Institute of Organic Chemistry, Lodz University of Technology, 90-924 Lodz, Poland.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Leonczak</LastName><ForeName>Piotr</ForeName><Initials>P</Initials><AffiliationInfo><Affiliation>Institute of Organic Chemistry, Lodz University of Technology, 90-924 Lodz, Poland.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wozniak</LastName><ForeName>Karolina</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Institute of Organic Chemistry, Lodz University of Technology, 90-924 Lodz, Poland.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Malkiewicz</LastName><ForeName>Andrzej</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Institute of Organic Chemistry, Lodz University of Technology, 90-924 Lodz, Poland.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>04</Month><Day>22</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>RNA</MedlineTA><NlmUniqueID>9509184</NlmUniqueID><ISSNLinking>1355-8382</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C540247">5-taurinomethyl-2-thiouridine</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000926">Anticodon</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009843">Oligoribonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012356">RNA, Transfer, Leu</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012357">RNA, Transfer, Lys</NameOfSubstance></Chemical><Chemical><RegistryNumber>13957-31-8</RegistryNumber><NameOfSubstance UI="D013891">Thiouridine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000926" MajorTopicYN="N">Anticodon</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="Y">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008928" MajorTopicYN="N">Mitochondria</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="Y">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009154" MajorTopicYN="N">Mutation</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009690" MajorTopicYN="N">Nucleic Acid Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009843" MajorTopicYN="N">Oligoribonucleotides</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012356" MajorTopicYN="N">RNA, Transfer, Leu</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="Y">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012357" MajorTopicYN="N">RNA, Transfer, Lys</DescriptorName><QualifierName UI="Q000235" 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first="Grazyna" last="Leszczynska">Grazyna Leszczynska</name></noRegion><name sortKey="Leonczak, Piotr" sort="Leonczak, Piotr" uniqKey="Leonczak P" first="Piotr" last="Leonczak">Piotr Leonczak</name><name sortKey="Malkiewicz, Andrzej" sort="Malkiewicz, Andrzej" uniqKey="Malkiewicz A" first="Andrzej" last="Malkiewicz">Andrzej Malkiewicz</name><name sortKey="Wozniak, Karolina" sort="Wozniak, Karolina" uniqKey="Wozniak K" first="Karolina" last="Wozniak">Karolina Wozniak</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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