Synthesis of Peptaibolin, an antimicrobial peptide
| Autor: | Susana P. G. Costa, Ana Ribeiro, Sílvia M. M. A. Pereira-Lima, Helena P. Felgueiras |
|---|---|
| Přispěvatelé: | Universidade do Minho |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
0209 industrial biotechnology
Engineering business.industry 010401 analytical chemistry Library science 02 engineering and technology Solid-phase approach 01 natural sciences 3. Good health 0104 chemical sciences 020901 industrial engineering & automation Peptide synthesis Engenharia e Tecnologia::Engenharia dos Materiais Bacteria resistance Antimicrobial peptides Engenharia dos Materiais [Engenharia e Tecnologia] Peptaibolin business |
| Zdroj: | Repositório Científico de Acesso Aberto de Portugal Repositório Científico de Acesso Aberto de Portugal (RCAAP) instacron:RCAAP |
| Popis: | To tackle one of the biggest global health problems, the resistance of microorganisms to antibiotics, a collective effort in the search for more effective agents against bacteria was required. Peptides with antimicrobial activity have been raising much attention as a promising alternative for antibiotics. Peptaibols, for instance, are a family of antimicrobial peptides (AMPs) with great biomedical potential, in which the Peptaibolin can be highlighted. This peptide has gained relevance due to its small amino acids content, only four, and its acetyl group and a phenylalaninol residue (Phol) at the N-terminal and C-terminal, respectively. Here, we report the synthesis of Peptaibolin through Solid Phase Peptide Synthesis assisted by Microwave heating (MW-SPPS) in a pre-loaded Phe-Wang resin. Starting from a loading of 0.51 mmol/g, two syntheses were made, using two different combinations of coupling reagents. The best option was DIC/Oxima, achieving a yield of 50.0%. Proton Nuclear Magnetic Resonance (1H-NMR) studies confirmed the peptide structure, while High Performance Liquid Chromatography (HPLC) verified the peptide purity. The peptide solubility was examined against several combinations of solvents. Peptaibolin was not soluble in water, only in organic solvents or in the combination of both. Antimicrobial testing was conducted using Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, and Pseudomonas aeruginosa. Minimum inhibitory concentration studies demonstrated the resistance of bacteria to the peptide action and the peptide instability in bacterial growth conditions Fundação para a Ciência e Tecnologia-FCT (Portugal) for funding through CQUM (UID/QUI/00686/2020) and project PTDC/QUI-COL/28052/2017. The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. Authors also acknowledge FCT for funding the project PEPTEX with reference PTDC/CTM-TEX/28074/2017 (POCI-01-0145-FEDER-028074). They acknowledge project UID/CTM/00264/2021 of Centre for Textile Science and Technology (2C2T), funded by national funds through FCT/MCTES |
| Databáze: | OpenAIRE |
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