Feasible Access to Large Peptidomimetic Macrocycles and Their Transmembrane Transportation Function

Abstract

Synthesis of macrocycles in general requires a template under ultra-dilution reaction condition. Inspired by our discovery of β-turn structure in the acylaminoacid based amidothiourea motif obtained from the reaction of the corresponding acylhydrazine and phenylisothiocyanate, that we propose to function as an in situ generated template for cyclization reaction, we developed a feasible way of synthesis of 46-membered large peptidomimetic macrocycles, starting from 2 molecules of 2,6-pyridinedicarbonylamino acid based acylhydrazine and 2 molecules of 1,4-benzenediisothiocyanate, with yields of ca. 60% under mild conditions after simple filtration. The method also applied well to other aryldiisothiocyanate, leading to macrocycles of even larger sizes. Part of those large macrocycles were found to form nano-channels exhibiting functions of transmembrane transportation for glucose, for example.

 

Biography

Dr. Yun-Bao Jiang was born in Anhui, China. He studied chemistry at Xiamen University with a PhD in 1990, after which he started his independent career in Department of Chemistry, Xiamen University, where he is currently a full professor. He did his postdoc researches at Max-Planck-Institut für biophysikalische Chemie, Göttingen, Germany and the University of Hong Kong. His research focuses on photoinduced electron/proton transfer and supramolecular spectral sensing and molecular recognition, from which he has published over 200 papers. He has been an invited professor at ENS Cachan, France, A RS short-term scientist at Southampton University, UK, a visiting professor at NUS, Singapore and a visiting scientist at NTU, Singapore. He was awarded the Alexander von Humboldt research fellowship and the distinguished young scholar grant of the NSF of China. Professor Jiang has been Vice Dean and Dean of the College of Chemistry and Chemical Engineering and currently Vice President of Xiamen University.