title: 2-Methyltetrahydrofuran and cyclopentyl methyl ether for green solid-phase peptide synthesis.
abstract: 2-MeTHF and CPME were evaluated as greener alternatives for the most employed 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 also determined. We concluded that the use of 2-MeTHF with combination of DIC/OxymaPure gave the lowest racemization level during stepwise synthesis of Z-Phg-Pro-NH2 and the highest purity during SPPS of Aib-enkephalin pentapeptide (H-Tyr-Aib-Aib-Phe-Leu-NH2).
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.affiliation: Institute for Research in Biomedicine-Barcelona, 08028, Barcelona, Spain.|CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028, Barcelona, Spain.
authors.forename: Gerardo A
authors.initials: GA
authors.lastname: Acosta
authors.affiliation: Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt.
authors.forename: Sherine N
authors.initials: SN
authors.lastname: Khattab
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa.
authors.forename: Beatriz G
authors.initials: BG
authors.lastname: de la Torre
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa.
authors.forename: Thavendran
authors.initials: T
authors.lastname: Govender
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa.
authors.forename: Hendrik G
authors.initials: HG
authors.lastname: Kruger
authors.affiliation: Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt. aymanel_faham@hotmail.com.|Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi Arabia. aymanel_faham@hotmail.com.
authors.forename: Ayman
authors.initials: A
authors.lastname: El-Faham
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban, 4001, South Africa. albericio@irbbarcelona.org.|Institute for Research in Biomedicine-Barcelona, 08028, Barcelona, Spain. albericio@irbbarcelona.org.|CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028, Barcelona, Spain. albericio@irbbarcelona.org.|Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi Arabia. albericio@irbbarcelona.org.|School of Chemistry and Physics, University of KwaZulu-Natal, Durban, 4001, South Africa. albericio@irbbarcelona.org.|Department of Organic Chemistry, University of Barcelona, 08028, Barcelona, Spain. albericio@irbbarcelona.org.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D015195:Drug Design; D005663:Furans / Q000737:chemistry*; D008738:Methyl Ethers / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D005663:Furans; D008738:Methyl Ethers; D010455:Peptides; C550584:2-methyltetrahydrofuran
keywords: 2-methyltetrahydrofuran; Cyclopentyl methyl ether; Green solvents; Peptide synthesis; Solid-phase peptide synthesis