title: Peptidomimetic bond formation by DNA-templated acyl transfer.
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.
authors.affiliation: Department of Physics, University of Oxford, Clarendon Laboratory, Parks Road, Oxford, United Kingdom OX1 3PU.
authors.forename: Mireya L
authors.initials: ML
authors.lastname: McKee
authors.forename: Amanda C
authors.initials: AC
authors.lastname: Evans
authors.forename: Simon R
authors.initials: SR
authors.lastname: Gerrard
authors.forename: Rachel K
authors.initials: RK
authors.lastname: O'Reilly
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Turberfield
authors.forename: Eugen
authors.initials: E
authors.lastname: Stulz
mesh_terms: D000588:Amines / Q000737:chemistry; D040761:Biomimetic Materials / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013696:Temperature
chemical_list: D000588:Amines; D009841:Oligonucleotides; D010455:Peptides; D013438:Sulfhydryl Compounds; D004247:DNA