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.
Highlights
Many high-yielding reactions for forming peptide bonds have been developed but these are complex, requiring activated amino-acid precursors and heterogeneous supports
We demonstrate an uncatalysed, amino acid oligomerization reaction producing unprecedentedly high yields of long oligomers using a very simple approach with a programmable reactor system allowing the exploration of many experimental parameters
Aqueous solutions of amino acid monomers were added to a hot empty glass vial and the water was removed by continuous heating
Summary
Many high-yielding reactions for forming peptide bonds have been developed but these are complex, requiring activated amino-acid precursors and heterogeneous supports. The peptide bonds that link together amino acids into short oligomers and proteins are vital for biology[1] Because of this biological importance, many high-yielding reactions for forming peptide bonds have been developed, but these typically require activated amino-acid precursors and heterogeneous supports[2]. Peptide bond formation has been widely established, obtaining oligopeptides in high yields requires catalysis, to overcome kinetic limitations, and activation of the amino acid monomers, to overcome thermodynamic limitations. We demonstrate an uncatalysed, amino acid oligomerization reaction producing unprecedentedly high yields of long oligomers using a very simple approach with a programmable reactor system allowing the exploration of many experimental parameters (see Supplementary Figs 1–6)
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