Γ-Valerolactone (GVL): An eco-friendly anchoring solvent for solid-phase peptide synthesis. Issue 38 (19th September 2019)

• Record Type: Journal Article
• Authors: Al Musaimi, Othman; El-Faham, Ayman; Basso, Alessandra; de la Torre, Beatriz G.; Albericio, Fernando
• Is Part Of: Tetrahedron letters. Volume 60:Issue 38(2019)
• Publication Date: 2019-09-19
• Subjects: Green chemistry -- Wang resin -- Racemization -- Dipeptide formation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151058
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Alternatives to the use of hazardous CH2 Cl2 are developed. γ-Valerolactone could replace CH2 Cl2 for loading the first amino acid onto Wang resin. An eco-friendly solid-phase peptide synthesis is proposed. Abstract: Due to the hazardous nature of CH2 Cl2, regulatory authorities have imposed restrictions to minimize or even stop its use. It has therefore become imperative to identify environmentally benign solvents to replace it. Here we report on a bio derived solvent, γ-valerolactone, for the incorporation of the first amino acid onto p-alkoxybenzyl alcohol resin in solid-phase peptide synthesis. Satisfactory loading values (by a spectrophotometric method) were achieved. Furthermore, racemization and dipeptide formation were also checked and found to be acceptable.