Solid-Phase Synthesis of Peptide Conjugates Derived from the Antimicrobial Cyclic Decapeptide BPC194
dc.contributor.author
dc.date.accessioned
2015-09-17T07:13:20Z
dc.date.available
2015-09-17T07:13:20Z
dc.date.issued
2015-02
dc.identifier.issn
1434-193X
dc.identifier.uri
dc.description.abstract
The solid-phase conjugation of the antimicrobial peptide c(KKLKKFKKLQ) (BPC194) to a linear or cyclic sequence through a 1,2,3-triazole ring is described. Cyclic alkynyl-peptidyl resins derived from BPC194 were treated with azidopeptides derived from the antimicrobial peptide BP100 or from the bacteriocin iturin A. The cyclic alkynyl-peptidyl resins incorporated at the 3-position a propargylglycine, a glutamic acid residue derivatized with propargylamine or a lysine bearing a propioloyl group. The reactions of the cyclic alkynyl resins with the BP100-derived azidopeptides depended on the length and the sequence of the azidopeptides. The reactions were performed by treatment of the alkynyl resin with CuI and ascorbic acid, and required the presence of piperidine/DMF or DIEA in 2,6-lutidine/DMF. The latter conditions also allowed the conjugation of the alkynyl-peptidyl resin bearing a propioloyl lysine to a linear or cyclic azidopeptide derived from the cyclic moiety of iturin A
dc.description.sponsorship
S. V. was recipient of a predoctoral fellowship from the Generalitat de Catalunya. This work was supported by the Spanish Ministerio de Economia y Competitividad (MINECO) (grant numbers AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02)
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
Wiley-VCH Verlag
dc.relation
info:eu-repo/grantAgreement/MINECO//AGL2012-39880-C02-02/ES/NUEVAS ESTRATEGIAS DE CONTROL DEL FUEGO BACTERIANO. PEPTIDOS SINTETICOS ESTIMULADORES DE DEFENSA EN EL HUESPED/
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02/ES/Control Biotecnologico Del Fuego Bacteriano. Utilizacion De Peptidos Antimicrobianos Sinteticos Derivados De Bacteriocinas Y De Ciclolipopeptidos/
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Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201403344
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© European Journal of Organic Chemistry, 2015, vol. 5, p. 1117-1129
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.subject
dc.title
Solid-Phase Synthesis of Peptide Conjugates Derived from the Antimicrobial Cyclic Decapeptide BPC194
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/embargoedAccess
dc.embargo.terms
Cap
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2026-01-01
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
022882
dc.contributor.funder
dc.relation.ProjectAcronym
dc.identifier.eissn
1099-0690