Ayman El-Faham
King Saud University, Saudi Arabia
Title: Green alternative solvents for peptide synthesis
Biography
Biography: Ayman El-Faham
Abstract
N,N-dimethylformamide (DMF) has been considered the only solvent suitable for peptide synthesis. Here we reported the use of 2-Methyltetrahydrofuran (2-MeTHF), cyclopentylmethyl ether (CPME),) tetrahydrofuran (THF) and acetonitrile (ACN) as greener alternative solvents in peptide synthesis. The ability of these solvents to dissolve amino acid derivatives and a range of coupling reagents were evaluated as well as the swelling of polystyrene and polyethylene glycol resins. In addition, racemization and coupling efficiencies were evaluated with a model of peptide (stepwise and segment coupling). The combination between 2-MeTHF as a solvent with DIC/OxymaPure as a coupling methodology gave the lowest racemization level during stepwise synthesis and the highest purity during SPPS of pentapeptide (Aib-enkephalin pentapeptide; H-Tyr-Aib-Aib-Phe-Leu-NH2). Moreover, the use of ACN and THF in the solid-phase peptide synthesis of hindered peptides, such as Aib-enkephaline pentapeptide and Aib-ACP decapeptide, in combination with the totally polyethylene glycol ChemMatrixresin, gave a better coupling efficiency than DMF.