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Solid-phase synthesis of cyclic lipopeptidotriazoles

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

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)

Wiley-VCH Verlag

Director: Ministerio de Ciencia e Innovación (Espanya)
Autor: Vilà Roura, Sílvia
Camó Marín, Cristina
Figueras, Eduard
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
Data: agost 2014
Resum: 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
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)
Format: application/pdf
Accés al document: http://hdl.handle.net/10256/10935
Llenguatge: eng
Editor: Wiley-VCH Verlag
Col·lecció: info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201402111
info:eu-repo/semantics/altIdentifier/issn/1434-193X
info:eu-repo/semantics/altIdentifier/eissn/1099-0690
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/
Drets: Tots els drets reservats
Matèria: Pèptids -- Síntesi
Peptides -- Synthesis
Compostos orgànics -- Síntesi
Organic compounds -- Synthesis
Compostos heterocíclics -- Síntesi
Heterocyclic compounds -- Synthesis
Títol: Solid-phase synthesis of cyclic lipopeptidotriazoles
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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