{ "dc.contributor.author": "Vilà Roura, Sílvia" , "dc.contributor.author": "Camó Marin, Cristina" , "dc.contributor.author": "Figueras, Eduard" , "dc.contributor.author": "Badosa Romañó, Esther" , "dc.contributor.author": "Montesinos Seguí, Emilio" , "dc.contributor.author": "Planas i Grabuleda, Marta" , "dc.contributor.author": "Feliu Soley, Lídia" , "dc.date.accessioned": "2015-09-17T07:23:48Z" , "dc.date.available": "2015-09-17T07:23:48Z" , "dc.date.issued": "2014-08" , "dc.identifier.issn": "1434-193X (versió paper)" , "dc.identifier.issn": "1099-0690 (versió electrònica)" , "dc.identifier.uri": "http://hdl.handle.net/10256/10935" , "dc.description.abstract": "The solid-phase synthesis of cyclic lipopeptidotriazoles derived from the cyclic decapeptide c(Lys-Lys(2)-Leu-Lys-Lys(5)-Phe-Lys-Lys-Leu-Gln) (BPC194), incorporating a triazolyl ring at Lys(2) and a hexanoyl group at Lys(5), was studied. Four different strategies that required the use of five orthogonal protecting groups (Fmoc, tBu, All, pNZ, ivDde) were explored. The influence of the side-chain protection of Lys(2) and Lys(5) with the ivDde and pNZ groups was evaluated by incorporating Lys(2)(ivDde)/Lys(5)(pNZ) or Lys(2)(pNZ)/Lys(5)(ivDde). The order of removal of these protecting groups and of the introduction of the hexanoyl and triazolyl moieties was also studied. The best strategy included: (i) synthesis of a cyclic peptidyl resin bearing Lys(2)(ivDde) and Lys(5)(pNZ); (ii) pNZ group removal; (iii) acylation with hexanoic acid; (iv) ivDde group removal; and (v) acylation with propiolic acid followed by an azide-alkyne 1,3-dipolar cycloaddition. By using this protocol, a set of cyclic lipopeptidotriazoles was prepared in high purities" , "dc.description.sponsorship": "S. V. is a recipient of a predoctoral fellowship from the Generalitat de Catalunya. This work was supported by grants from the Spanish Ministerio de Economia y Competitividad (MINECO) (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": "MICINN/PN 2013-2015/AGL2012-39880-C02-02" , "dc.relation": "MICINN/PN 2010-2012/AGL2009-13255-C02-02" , "dc.relation.isformatof": "Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201402111" , "dc.relation.ispartof": "© European Journal of Organic Chemistry, 2014, vol. 22, p. 4785-4794" , "dc.relation.ispartofseries": "Articles publicats (D-Q)" , "dc.rights": "Tots els drets reservats" , "dc.subject": "Pèptids -- Síntesi" , "dc.subject": "Peptides -- Synthesis" , "dc.subject": "Compostos orgànics -- Síntesi" , "dc.subject": "Organic compounds -- Synthesis" , "dc.subject": "Compostos heterocíclics -- Síntesi" , "dc.subject": "Heterocyclic compounds -- Synthesis" , "dc.title": "Solid-phase synthesis of cyclic lipopeptidotriazoles" , "dc.type": "info:eu-repo/semantics/article" , "dc.rights.accessRights": "info:eu-repo/semantics/embargoedAccess" , "dc.embargo.terms": "Cap" , "dc.type.version": "info:eu-repo/semantics/publishedVersion" , "dc.identifier.doi": "http://dx.doi.org/10.1002/ejoc.201402111" , "dc.identifier.idgrec": "021451" , "dc.contributor.funder": "Ministerio de Ciencia e Innovación (Espanya)" }