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Issue 5, 2011
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Peptidomimetic bond formation by DNA-templated acyl transfer

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Abstract

The efficiencies of DNA-templated acyl transfer reactions between a thioester modified oligonucleotide and a series of amine and thiol based nucleophiles are directly compared. The reactivity of the nucleophile, reaction conditions (solvent, buffer, pH) and linker length all play important roles in determining the efficiency of the transfer reaction. Careful optimisation of the system enables the use of DNA-templated synthesis to form stable peptide-like bonds under mild aqueous conditions close to neutral pH.

Graphical abstract: Peptidomimetic bond formation by DNA-templated acyl transfer

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Article information


Submitted
20 Sep 2010
Accepted
23 Nov 2010
First published
24 Nov 2010

Org. Biomol. Chem., 2011,9, 1661-1666
Article type
Paper

Peptidomimetic bond formation by DNA-templated acyl transfer

M. L. McKee, A. C. Evans, S. R. Gerrard, R. K. O'Reilly, A. J. Turberfield and E. Stulz, Org. Biomol. Chem., 2011, 9, 1661
DOI: 10.1039/C0OB00753F

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