Chi Zhang; Yizhou Li; Mingda Zhang; Xiaoyu Li
Tetrahedron, 2012, 68, 5152-5156
https://doi.org/10.1016/j.tet.2012.04.032

Abstract

A model study of DNA-directed peptide ligation has been developed by transferring fluorescent reporting group from small molecule thioester to a DNA strand (template DNA) in the presence of a thiolfunctionalized DNA strand (auxiliary DNA), mimicking the Native Chemical Ligation (NCL) reaction.
This DNA-directed transfer shows dependence on the sequence complementarity of the two DNA strands, with in situ generated 4-thiolphenylmethyl functionalized oligonucleotide as the auxiliary DNA strand, under mild basic condition (pH¼8.5), and with tris(2-carboxyethyl) phosphine hydrochloride (TCEP) as a reducing agent. Reactions with different amino acid a-thioesters resulted in varied transfer efficiencies from glycine to a-substituted amino acids. This study has provided the basic foundation to use DNA-programmed chemistry toward the chemical synthesis or unnatural modification of protein molecules.