Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.
Identifieur interne : 001632 ( PubMed/Corpus ); précédent : 001631; suivant : 001633Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.
Auteurs : Alberto Oddo ; Lena Münzker ; Paul R. HansenSource :
- Organic letters [ 1523-7052 ] ; 2015.
English descriptors
- KwdEn :
- Amino Acid Sequence, Antimicrobial Cationic Peptides (chemical synthesis), Antimicrobial Cationic Peptides (chemistry), Molecular Structure, Peptides (chemical synthesis), Peptides (chemistry), Peptides, Cyclic (chemical synthesis), Peptides, Cyclic (chemistry), Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
- MESH :
- chemical , chemical synthesis : Antimicrobial Cationic Peptides, Peptides, Peptides, Cyclic.
- chemical , chemistry : Antimicrobial Cationic Peptides, Peptides, Peptides, Cyclic.
- Amino Acid Sequence, Molecular Structure, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
Abstract
A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.
DOI: 10.1021/acs.orglett.5b01026
PubMed: 25923311
Links to Exploration step
pubmed:25923311Le document en format XML
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Hansen</name><affiliation><nlm:affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2015">2015</date><idno type="RBID">pubmed:25923311</idno><idno type="pmid">25923311</idno><idno type="doi">10.1021/acs.orglett.5b01026</idno><idno type="wicri:Area/PubMed/Corpus">001632</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001632</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.</title><author><name sortKey="Oddo, Alberto" sort="Oddo, Alberto" uniqKey="Oddo A" first="Alberto" last="Oddo">Alberto Oddo</name><affiliation><nlm:affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</nlm:affiliation></affiliation></author><author><name sortKey="Munzker, Lena" sort="Munzker, Lena" uniqKey="Munzker L" first="Lena" last="Münzker">Lena Münzker</name><affiliation><nlm:affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</nlm:affiliation></affiliation></author><author><name sortKey="Hansen, Paul R" sort="Hansen, Paul R" uniqKey="Hansen P" first="Paul R" last="Hansen">Paul R. Hansen</name><affiliation><nlm:affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Organic letters</title><idno type="eISSN">1523-7052</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term><term>Antimicrobial Cationic Peptides (chemical synthesis)</term><term>Antimicrobial Cationic Peptides (chemistry)</term><term>Molecular Structure</term><term>Peptides (chemical synthesis)</term><term>Peptides (chemistry)</term><term>Peptides, Cyclic (chemical synthesis)</term><term>Peptides, Cyclic (chemistry)</term><term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antimicrobial Cationic Peptides</term><term>Peptides</term><term>Peptides, Cyclic</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimicrobial Cationic Peptides</term><term>Peptides</term><term>Peptides, Cyclic</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term><term>Molecular Structure</term><term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25923311</PMID><DateCompleted><Year>2015</Year><Month>10</Month><Day>05</Day></DateCompleted><DateRevised><Year>2015</Year><Month>05</Month><Day>15</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1523-7052</ISSN><JournalIssue CitedMedium="Internet"><Volume>17</Volume><Issue>10</Issue><PubDate><Year>2015</Year><Month>May</Month><Day>15</Day></PubDate></JournalIssue><Title>Organic letters</Title><ISOAbbreviation>Org. Lett.</ISOAbbreviation></Journal><ArticleTitle>Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.</ArticleTitle><Pagination><MedlinePgn>2502-5</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.orglett.5b01026</ELocationID><Abstract><AbstractText>A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Oddo</LastName><ForeName>Alberto</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Münzker</LastName><ForeName>Lena</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hansen</LastName><ForeName>Paul R</ForeName><Initials>PR</Initials><AffiliationInfo><Affiliation>Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.</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>2015</Year><Month>04</Month><Day>29</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Org Lett</MedlineTA><NlmUniqueID>100890393</NlmUniqueID><ISSNLinking>1523-7052</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D023181">Antimicrobial Cationic Peptides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010455">Peptides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010456">Peptides, Cyclic</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000595" MajorTopicYN="N">Amino Acid Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D023181" MajorTopicYN="N">Antimicrobial Cationic Peptides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010455" MajorTopicYN="N">Peptides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010456" MajorTopicYN="N">Peptides, Cyclic</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D019032" MajorTopicYN="N">Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>4</Month><Day>30</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>4</Month><Day>30</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>10</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25923311</ArticleId><ArticleId IdType="doi">10.1021/acs.orglett.5b01026</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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