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A New Approach to Obtaining N ?-t-Boc-Amino Acid Aldehydes from Asparagine and Glutamine for Reduced Amide Pseudopeptide Solid-Phase Synthesis

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dc.creatorCarreño L.F.spa
dc.creatorAlba M.P.spa
dc.creatorVarela Y.spa
dc.creatorPatarroyo M.E.spa
dc.creatorLozano J.M.spa
dc.date.accessioned2020-05-26T00:04:01Z
dc.date.available2020-05-26T00:04:01Z
dc.date.created2011spa
dc.description.abstractReduced amide pseudopeptides have been proposed as structural probes that could be useful as potential malarial vaccine components. However, designing determined pseudopeptide sequences containing isoster peptide bonds, either on an asparagine (Asn) or on a glutamine (Gln) residues, can become difficult because these precursor amino acid aldehydes are obtained in yields lower than 0.5%. This work presents a new strategy for obtaining both Asn and Gln aldehydes based on a controlled side-chain protection approach as well as a suitable solvent partition procedure. FT-IR, 1H-NMR and 13C-NMR were used for molecule characterization and identification. Amino acid aldehydes were successfully incorporated into a 20-mer peptide from a malarial-relevant sequence, and their impact on the molecule's conformational properties was assessed. Reduced amide isoster-bond pseudopeptides are regarded as potential components for a sub-unit based malarial vaccine. However, sequences containing isoster bonds involving asparagine or glutamine can become difficult since these precursors are obtained in yields lower than 0.5%. The current report presents a new controlled side-chain protection strategy for obtaining both aldehydes in yields higher than 80%. These synthons were successfully incorporated into malarial-relevant 20-mer peptides and their impact on the molecule's conformational properties was assessed. The MSP-1 202-221peptide 1522 native sequence in the upper and its ?-14411 analog harboring the ( 206Asn-CH 2-NH-Leu 207) isoster bond is shown at the bottom. © 2011 John Wiley and amp; Sons A/S.eng
dc.format.mimetypeapplication/pdf
dc.identifier.doihttps://doi.org/10.1111/j.1747-0285.2011.01182.x
dc.identifier.issn17470277
dc.identifier.urihttps://repository.urosario.edu.co/handle/10336/23649
dc.language.isoengspa
dc.relation.citationEndPage611
dc.relation.citationIssueNo. 4
dc.relation.citationStartPage603
dc.relation.citationTitleChemical Biology and Drug Design
dc.relation.citationVolumeVol. 78
dc.relation.ispartofChemical Biology and Drug Design, ISSN:17470277, Vol.78, No.4 (2011); pp. 603-611spa
dc.relation.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-80052623680&doi=10.1111%2fj.1747-0285.2011.01182.x&partnerID=40&md5=4cc3a1d11e89bb3e4900e09dc621a936spa
dc.rights.accesRightsinfo:eu-repo/semantics/openAccess
dc.rights.accesoAbierto (Texto Completo)spa
dc.source.instnameinstname:Universidad del Rosariospa
dc.source.reponamereponame:Repositorio Institucional EdocURspa
dc.subject.keywordAminoaldehydespa
dc.subject.keywordAsparagine derivativespa
dc.subject.keywordDichloromethanespa
dc.subject.keywordGlutamine derivativespa
dc.subject.keywordPseudopeptidespa
dc.subject.keywordTetrahydrofuranspa
dc.subject.keywordArticlespa
dc.subject.keywordCarbon nuclear magnetic resonancespa
dc.subject.keywordCircular dichroismspa
dc.subject.keywordConformationspa
dc.subject.keywordInfrared spectroscopyspa
dc.subject.keywordPhase partitioningspa
dc.subject.keywordPriority journalspa
dc.subject.keywordProton nuclear magnetic resonancespa
dc.subject.keywordSolid phase synthesisspa
dc.subject.keywordStructure activity relationspa
dc.subject.keywordThin layer chromatographyspa
dc.subject.keywordAldehydesspa
dc.subject.keywordAmidesspa
dc.subject.keywordAsparaginespa
dc.subject.keywordGlutaminespa
dc.subject.keywordOxidation-reductionspa
dc.subject.keywordSolid-phase synthesis techniquesspa
dc.subject.keywordAmino acidspa
dc.subject.keywordNmr-spectroscopyspa
dc.subject.keywordPeptidomimeticspa
dc.subject.keywordPseudopeptidespa
dc.subject.keywordVaccine candidatespa
dc.titleA New Approach to Obtaining N ?-t-Boc-Amino Acid Aldehydes from Asparagine and Glutamine for Reduced Amide Pseudopeptide Solid-Phase Synthesisspa
dc.typearticleeng
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersion
dc.type.spaArtículospa
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