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Formation of oligopeptides in high yield under simple programmable conditions

Author

Listed:
  • 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)

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.

Suggested Citation

  • Marc Rodriguez-Garcia & Andrew J. Surman & Geoffrey J.T. Cooper & Irene Suárez-Marina & Zied Hosni & Michael P. Lee & Leroy Cronin, 2015. "Formation of oligopeptides in high yield under simple programmable conditions," Nature Communications, Nature, vol. 6(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms9385
    DOI: 10.1038/ncomms9385
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    Cited by:

    1. Fabian Sauer & Maren Haas & Constanze Sydow & Alexander F. Siegle & Christoph A. Lauer & Oliver Trapp, 2021. "From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    2. Peiying Li & Philipp Holliger & Shunsuke Tagami, 2022. "Hydrophobic-cationic peptides modulate RNA polymerase ribozyme activity by accretion," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

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