Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/39800

TitlePeptaibolin analogues by incorporation of α,α-dialkylglycines: synthesis and study of their membrane permeating ability
Author(s)Castro, Vânia I. B.
Carvalho, Carina Martins
Fernandes, Rui D. V.
Pereira-Lima, Sílvia M. M. A.
Castanheira, Elisabete M. S.
Costa, Susana P. G.
Keywordsalpha,alpha-Dialkylglycines
Peptaibolin
Membrane permeating peptides
Model membranes
Fluorescence spectroscopy
Issue dateJan-2016
PublisherElsevier
JournalTetrahedron
CitationV. I. B. Castro, C. M. Carvalho, R. D. V. Fernandes, S. M. M. A. Pereira-Lima, E. M. S. Castanheira, S. P. G. Costa, “Peptaibolin analogues by incorporation of α,α-dialkylglycines: synthesis and study of their membrane permeating ability”, Tetrahedron, 2016, 72, 1024-1030.
Abstract(s)Analogues of Peptaibolin, a peptaibol with antibiotic activity, incorporating α,α-dialkylglycines (Deg, Dpg, and Ac6c) at selected positions were synthesised by MW-SPPS and fully characterized. A control analogue incorporating L-alanine was also prepared. The native peptide and the analogues were studied by fluorescence spectroscopy for their membrane permeating activity. Small unilamellar vesicles (SUVs) of egg phosphatidylcholine/ cholesterol (70:30) containing an encapsulated fluorescence probe (6-carboxyfluorescein) were used as membrane models. The assays of carboxyfluorescein release from SUVs upon peptide addition showed that Peptaibolin-Dpg and Peptaibolin-Ac6c are the most active peptides. These results indicate that the structure of the α,α-dialkylglycines is crucial for the membrane permeating ability of these Peptaibolin analogues.
TypeArticle
URIhttp://hdl.handle.net/1822/39800
DOI10.1016/j.tet.2015.12.079
ISSN0040-4020
Publisher versionhttp://dx.doi.org/10.1016/j.tet.2015.12.079
Peer-Reviewedyes
AccessRestricted access (Author)
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)
CDQuim - Artigos (Papers)

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