Development of a Linker with an Enhanced Stability for the Preparation of Peptide Thioesters and Its Application to the Synthesis of a Stable-Isotope-Labelled HU-Type DNA-Binding Protein

Article abstract of DOI:10.1246/bcsj.66.2700

An S-alkyl-thioester-moiety-containing linker with an enhanced stability on a resin has been developed.A linker containing S-alkyl thioester with a spacer group, -CO-SC(CH3)2CH2CO-Nle-, was stable during the peptide chain elongation cycle.This thioester was stable under HF treatment conditions, and was rapidly activated by silver ions in the presence of N-hydroxysuccinimde (HONSu) to form a peptide bond.Using this linker, peptide segments covering the HU-type DNA-binding protein of Bacillus stearothermophilus (HBs), which was site-specifically labelled with 2H, 13C,and 15N, were prepared.Using these peptide segments, multi-labelled HBs was synthesized.Distinct signals of 2H, 13C, and 15N in HBs were detected by NMR spectrometry.