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Formation of oligopeptides in high yield under simple programmable conditions

Marc Rodriguez-Garcia, Andrew J. Surman, Geoffrey J.T. Cooper, Irene Suárez-Marina, Zied Hosni, Michael P. Lee and Leroy Cronin ()
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Marc Rodriguez-Garcia: WestCHEM, School of Chemistry, University of Glasgow
Andrew J. Surman: WestCHEM, School of Chemistry, University of Glasgow
Geoffrey J.T. Cooper: WestCHEM, School of Chemistry, University of Glasgow
Irene Suárez-Marina: WestCHEM, School of Chemistry, University of Glasgow
Zied Hosni: WestCHEM, School of Chemistry, University of Glasgow
Michael P. Lee: WestCHEM, School of Chemistry, University of Glasgow
Leroy Cronin: WestCHEM, School of Chemistry, University of Glasgow

Nature Communications, 2015, vol. 6, issue 1, 1-7

Abstract: 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.

Date: 2015
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DOI: 10.1038/ncomms9385

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