Total solid-phase synthesis of dehydroxy fengycin derivatives
dc.contributor.author
dc.date.accessioned
2019-01-18T12:03:04Z
dc.date.available
2021-04-07T08:03:00Z
dc.date.issued
2018-12-10
dc.identifier.issn
0022-3263
dc.identifier.uri
dc.description.abstract
A rapid and efficient solid-phase strategy for the synthesis of dehydroxy fengycins derivatives is described. This synthetic approach involved the linkage of a Tyr to a Wang resin via a Mitsunobu reaction and the elongation of the peptide sequence followed by subsequent acylation of the N-terminus of the resulting linear peptidyl resin, esterification of the phenol group of a Tyr with an Ile, and final macrolactamization. The amino acid composition as well as the presence of the N-terminal acyl group significantly influenced the stability of the macrolactone. Cyclic lipodepsipeptides with a l-Tyr3/d-Tyr9 configuration were more stable than those containing the Tyr residues with an opposite configuration. This work constitutes the first approach on the total solid-phase synthesis of dehydroxy fengycin derivatives
dc.description.sponsorship
C.R. was the recipient of a predoctoral fellowship from the MINECO of Spain. This work was financed by grants AGL2012-39880-C02-02, AGL2015-69876-C2-2-R (MINECO/FEDER, EU) and MPCUdG2016/038. The authors acknowledge the Serveis Tècnics de Recerca of the University of Girona for the mass spectrometry analysis and the NMR experiments
dc.format.extent
15 p.
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
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/MINECO//AGL2015-69876-C2-2-R/ES/PEPTIDOS CONJUGADOS PARA EL CONTROL DE BACTERIAS FITOPATOGENAS DE CUARENTENA/
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Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.8b02553
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© Journal of Organic Chemistry, 2018, vol. 83, núm. 24, p. 15297-15311
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.source
Rosés, Cristina Camó Marin, Cristina Oliveras Rovira, Àngel Moll, Lluís López, Nerea Feliu Soley, Lídia Planas i Grabuleda, Marta 2018 Total solid-phase synthesis of dehydroxy fengycin derivatives Journal of Organic Chemistry 83 24 15297 15311
dc.subject
dc.title
Total solid-phase synthesis of dehydroxy fengycin derivatives
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
2019-12-10T00:00:00Z
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2019-12-10
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
029182
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
dc.relation.ProjectAcronym
dc.identifier.eissn
1520-6904