Formation of oligopeptides in high yield under simple programmable conditions

Rodriguez-Garcia, M., Surman, A. J. , Cooper, G. J.T. , Suarez Marina, I., Hosni, Z., Lee, M. P. and Cronin, L. (2015) Formation of oligopeptides in high yield under simple programmable conditions. Nature Communications, 6, 8385. (doi:10.1038/ncomms9385) (PMID:26442968) (PMCID:PMC4633627)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Cooper, Dr Geoff and Lee, Mr Michael and Suarez Marina, Irene and Cronin, Professor Lee and Hosni, Mr Zied and Surman, Dr Andrew
Authors: Rodriguez-Garcia, M., Surman, A. J., Cooper, G. J.T., Suarez Marina, I., Hosni, Z., Lee, M. P., and Cronin, L.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Nature Communications
Publisher:Nature Publishing Group
ISSN:2041-1723
ISSN (Online):2041-1723
Copyright Holders:Copyright © 2015 Macmillan Publishers Limited
First Published:First published in Nature Communications 6:8385
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
503291Molecular-Metal-Oxide-nanoelectronicS (M-MOS): Achieving the Molecular LimitLeroy CroninEngineering & Physical Sciences Research Council (EPSRC)EP/H024107/1CHEM - CHEMISTRY
503295Molecular-Metal-Oxide-nanoelectronicS (M-MOS): Achieving the Molecular LimitLeroy CroninEngineering & Physical Sciences Research Council (EPSRC)EP/H024107/1CHEM - CHEMISTRY
562821Innovative Manufacturing Research Centre for Continuous Manufacturing and Crystallisation (CMAC)Leroy CroninEngineering & Physical Sciences Research Council (EPSRC)EP/I033459/1CHEM - CHEMISTRY
577391Programmable Molecular Metal Oxides (PMMOs) - From Fundamentals to ApplicationLeroy CroninEngineering & Physical Sciences Research Council (EPSRC)EP/J015156/1CHEM - CHEMISTRY