title: Formation of oligopeptides in high yield under simple programmable conditions.
abstract: Many high-yielding reactions for forming peptide bonds have been developed but these are complex, requiring activated amino-acid precursors and heterogeneous supports. Herein we demonstrate the programmable one-pot dehydration-hydration condensation of amino acids forming oligopeptide chains in around 50% yield. A digital recursive reactor system was developed to investigate this process, performing these reactions with control over parameters such as temperature, number of cycles, cycle duration, initial monomer concentration and initial pH. Glycine oligopeptides up to 20 amino acids long were formed with very high monomer-to-oligomer conversion, and the majority of these products comprised three amino acid residues or more. Having established the formation of glycine homo-oligopeptides, we then demonstrated the co-condensation of glycine with eight other amino acids (Ala, Asp, Glu, His, Lys, Pro, Thr and Val), incorporating a range of side-chain functionality.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Marc
authors.initials: M
authors.lastname: Rodriguez-Garcia
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Surman
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Geoffrey J T
authors.initials: GJT
authors.lastname: Cooper
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Irene
authors.initials: I
authors.lastname: Suárez-Marina
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Zied
authors.initials: Z
authors.lastname: Hosni
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Michael P
authors.initials: MP
authors.lastname: Lee
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK.
authors.forename: Leroy
authors.initials: L
authors.lastname: Cronin
mesh_terms: D000596:Amino Acids; D001331:Automation; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D013058:Mass Spectrometry; D009842:Oligopeptides / Q000138:chemical synthesis*; D055601:Organic Chemistry Phenomena
chemical_list: D000596:Amino Acids; D009842:Oligopeptides