Related Experiment Video
Updated: Jul 5, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester
Hironobu Hojo1, Yuichi Murasawa, Hidekazu Katayama
1Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa 259-1292, Japan. hojo@keyaki.cc.u-tokai.ac.jp
Abstract:
Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag(+)-free thioester method.
More Related Videos
Related Concept Videos
Esters to β-Ketoesters: Claisen Condensation Mechanism
Esters to β-Ketoesters: Claisen Condensation Overview
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Preparation and Reactions of Thiols
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

