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Issue 7, 2014
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Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation

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Abstract

A new strategy is described to generate bicyclic peptides that incorporate non-peptidic backbone elements starting from recombinant polypeptide precursors. These compounds are produced via a one-pot, two-step sequence, in which peptide macrocyclization by means of a bifunctional oxyamine/1,3-amino-thiol synthetic precursor is followed by intramolecular disulfide formation between the synthetic precursor-borne thiol and a cysteine embedded in the peptide sequence. This approach was found to be compatible with the cysteine residue occupying different positions within 8mer and 10mer target peptide sequences and across different synthetic precursor scaffolds, thereby enabling the formation of a variety of diverse bicyclic scaffolds.

Graphical abstract: Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation

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Supplementary files

Article information


Submitted
09 Nov 2013
Accepted
18 Dec 2013
First published
07 Jan 2014

Org. Biomol. Chem., 2014,12, 1135-1142
Article type
Paper
Author version available

Synthesis of bicyclic organo-peptide hybrids via oxime/intein-mediated macrocyclization followed by disulfide bond formation

J. M. Smith, N. C. Hill, P. J. Krasniak and R. Fasan, Org. Biomol. Chem., 2014, 12, 1135
DOI: 10.1039/C3OB42222D

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