Green alternative solvents for peptide synthesis

European Chemistry Congress

June 16-18, 2016 Rome, Italy

Ayman El-Faham, Yahya E Jad, Gerardo A Acosta, Sherine N Khattab, Beatriz G de la Torre, Thavendran Govender, Hendrik G Kruger and Fernando Albericio

King Saud University, Saudi Arabia
University of Kwazulu-Natal, South Africa
Institute for Research in Biomedicine-Barcelona, Spain
Alexandria University, Egypt
Yachay City of Knowledge, Ecuador
University of Barcelona, Spain

Posters & Accepted Abstracts: Chem Sci J

Abstract :

To date, 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-AibAib-Phe-Leu-NH2). Moreover, the use of ACN and THF in the solid-phase peptide synthesis of hindered peptides, such as Aibenkephaline pentapeptide and Aib-ACP decapeptide, in combination with the totally polyethylene glycol ChemMatrixresin, gave a better coupling efficiency than DMF. aelfaham@ksu.edu.sa