118389
PTDC/QUI-BIQ/118389/2010
FCT - Fundação para a Ciência e a Tecnologia, I.P.
Portugal
5876-PPCDTI
99,330.00 €
2012-03-01
2015-08-31
We present a systematic study on the best conditions to achieve the microwave-assisted solid phase peptide synthesis of a selected peptaibol, namely the pentapeptide Peptaibolin (Ac-Leu-Aib-Leu-Aib-Phol), by using several resins and different coupling and cleavage conditions aiming at a future synthesis of mimetics of larger members of the peptaibol family bearing bulkier unnatural α,α-dialkylglycines.
Comunicação em painel PC82.; We report our research on the synthesis of the shortest Peptaibol, Peptaibolin (Ac-Leu-Aib-Leu-Aib-Phol) and several mimetics incorporating unnatural α,α-dialkylglycines at the Aib positions, using microwave-assisted solid phase peptide synthesis performed on a CEM discover SPS device.
Comunicação em painel PC139.; We report the conformational studies on a model peptide, Peptaibolin (Ac-Leu-Aib-Leu-Aib-Phol) and its mimetics incorporating unnatural α,α-dialkylglycines bearing longer and bulkier side chains in order to gain insight about the conformational preferences resulting from substitution of the native Aib residues. An Ala analogue was studied as a control in the conformational study. T...
Comunicação em painel P3; The membrane permeabilization ability of a model peptaibol and several mimetics incorporating unnatural α,α- dialkylglycines were studied by fluorescence spectroscopy. The model membranes (egg phosphatidylcholine/cholesterol, 70:30) contained a fluorescent probe encapsulated. By addition of peptides at different peptide to lipid ratios, it was possible to follow the release of the enca...
Comunicação em painel P60 no 2nd Symposium on Medicinal Chemistry, Braga, Portugal, 8 Maio 2015; It is reported the membrane permeation studies of Peptaibolin and several mimetics incorporating unnatural α,α-dialkylglycines (Deg, Dpg, Ac6c) with model membranes (egg phosphatidylcholine/cholesterol, in different ratios). The permeation activity was monitored by fluorescence spectroscopy, following release of an ...
In the present communication, a set of Peptaibolin and several peptidomimetics incorporating unnatural α,α-dialkylglycines (Deg, Dpg, Ac6c) were studied for their ability to interact and permeate model membranes from phosphatidylcholine/cholesterol, in different ratios. The permeation activity was monitored by fluorescence spectroscopy, following the release of encapsulated 6-carboxyfluorescein.; Fundação para ...
Comunicação oral OC19 no XV EPI- Iberian Peptide Meeting, Porto, Portugal, 10-12 Fevereiro 2016.; It is reported the membrane permeation studies of a model peptide, Peptaibolin (Ac-Leu-Aib-Leu-Aib-Phol), which is the shortest member of the peptaibols family, and several mimetics incorporating unnatural α,α- dialkylglycines (Deg, Dpg, Ac6c) at the native Aib positions. The model membranes were based on small uni...
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 eg...
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