Green solid-phase peptide synthesis 4. γ-Valerolactone and N-formylmorpholine as green solvents for solid phase peptide synthesis. Issue 30 (26th July 2017)

• Record Type: Journal Article
• Authors: Kumar, Ashish; Jad, Yahya E.; El-Faham, Ayman; de la Torre, Beatriz G.; Albericio, Fernando
• Is Part Of: Tetrahedron letters. Volume 58:Issue 30(2017)
• Page Start: 2986
• Page End: 2988
• Publication Date: 2017-07-26
• Subjects: Solid-phase peptide synthesis -- Green solvents -- Polystyrene resin -- GVL -- NFM; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.058
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Green SPPS strategy using polystyrene (PS) resin. GVL and NFM as excellent DMF substitutes in SPPS. Solubility of reagents studied in GVL and NFM. SPPS of Aib-enkephalin pentapeptide and Aib-ACP decapeptide using GVL and NFM. Abstract: Herein, we report the use of γ-valerolactone (GVL) and N -formylmorpholine (NFM) as DMF substitutes in polystyrene based SPPS. The solubility of selected amino acids and coupling reagents were studied in GVL and NFM, followed by their use in the successful synthesis of Aib-enkephalin pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2 ) and Aib-ACP decapeptide (H-Val-Gln-Aib-Aib-Ile-Asp-Tyr-Ile-Asn-Gly-NH2 ).