McKee, Mireya L., Evans, Amanda C., Gerrard, Simon R., O'Reilly, Rachel K., Turberfield, Andrew J. and Stulz, Eugen (2011) Peptidomimetic bond formation by DNA-templated acyl transfer. Organic & Biomolecular Chemistry, Vol.9 (No.5). pp. 1661-1666. doi:10.1039/c0ob00753f ISSN 1477-0520.

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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.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH):	Peptides, Biochemical templates, Acylation, Chemical bonds, Biosynthesis, Nucleophilic reactions
Journal or Publication Title:	Organic & Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Official Date:	2011
Dates:	Date Event 2011 UNSPECIFIED
Volume:	Vol.9
Number:	No.5
Page Range:	pp. 1661-1666
DOI:	10.1039/c0ob00753f
Status:	Peer Reviewed
Publication Status:	Published
Funder:	Engineering and Physical Sciences Research Council (EPSRC)
Grant number:	EP/F056605/1 (EPSRC), EP/008597/1 (EPSRC)

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