Peptidomimetic bond formation by DNA-templated acyl transfer

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-01, Vol.9 (5), p.1661-1666
Main Authors: McKee, Mireya L, Evans, Amanda C, Gerrard, Simon R, O'Reilly, Rachel K, Turberfield, Andrew J, Stulz, Eugen
Format: Article
Language:English
Subjects:
Amines - chemistry
Biomimetic Materials - chemistry
DNA - chemistry
Hydrogen-Ion Concentration
Hydrophobic and Hydrophilic Interactions
Molecular Structure
Oligonucleotides - chemistry
Peptides - chemistry
Sulfhydryl Compounds - chemistry
Temperature
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00753f