title: Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives.
abstract: 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.
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa.
authors.forename: Yahya E
authors.initials: YE
authors.lastname: Jad
authors.forename: Gerardo A
authors.initials: GA
authors.lastname: Acosta
authors.forename: Sherine N
authors.initials: SN
authors.lastname: Khattab
authors.forename: Beatriz G
authors.initials: BG
authors.lastname: de la Torre
authors.forename: Thavendran
authors.initials: T
authors.lastname: Govender
authors.forename: Hendrik G
authors.initials: HG
authors.lastname: Kruger
authors.forename: Ayman
authors.initials: A
authors.lastname: El-Faham
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000097:Acetonitriles / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D005663:Furans; D010455:Peptides; C018674:tetrahydrofuran; D004126:Dimethylformamide; C032159:acetonitrile