Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives.

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

Organic & biomolecular chemistry 2015 Feb 28

filter terms:

To date, DMF has been considered as the only solvent suitable for peptide synthesis. Here we demonstrate the capacity of THF and ACN, which are friendlier solvents than DMF, to yield the product in higher purity than DMF. Using various peptide models, both THF and ACN reduced racemization in solution-phase and solid-phase synthesis when compared with DMF. Moreover, the use of ACN and THF in the solid-phase peptide synthesis of hindered peptides, such as Aib-enkephalin pentapeptide and Aib-ACP decapeptide, in combination with a complete polyethylene glycol resin (ChemMatrix), gave a better coupling efficiency than DMF.

Citation

Yahya E Jad, Gerardo A Acosta, Sherine N Khattab, Beatriz G de la Torre, Thavendran Govender, Hendrik G Kruger, Ayman El-Faham, Fernando Albericio. Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives. Organic & biomolecular chemistry. 2015 Feb 28;13(8):2393-8