Article (Scientific journals)
Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides
Ollivier, Nathalie; Toupy, Thomas; Hartkoorn, Ruben et al.
2018In Nature Communications, 9, p. 2847
Peer Reviewed verified by ORBi
 

Files


Full Text
18N.pdf
Publisher postprint (821.43 kB)
Download

All documents in ORBi are protected by a user license.

Send to



Details



Keywords :
Native Chemical Ligation; Cyclic peptides; Microfluidics; Continuous Flow
Abstract :
[en] Cyclic peptide-based therapeutics have a promising growth forecast that justifies the development of microfluidic systems dedicated to their production, in phase with the actual transitioning toward continuous flow and microfluidic technologies for pharmaceutical production. The application of the most popular method for peptide cyclization in water, i.e., native chemical ligation, under microfluidic conditions is still unexplored. Herein, we report a general strategy for fast and efficient peptide cyclization using native chemical ligation under homogeneous microfluidic conditions. The strategy relies on a multistep sequence that concatenates the formation of highly reactive S-(2-((2-sulfanylethyl)amino)ethyl) peptidyl thioesters from stable peptide amide precursors with an intramolecular ligation step. With very fast ligation rates (<5 min), even for the most difficult junctions (including threonine, valine, isoleucine, or proline), this technology opens the door toward the scale-independent, expedient preparation of bioactive macrocyclic peptides.
Disciplines :
Chemistry
Author, co-author :
Ollivier, Nathalie 
Toupy, Thomas  ;  Université de Liège - ULiège > Département de chimie (sciences) > CITOS
Hartkoorn, Ruben
Desmet, Rémi
Monbaliu, Jean-Christophe   ;  Université de Liège - ULiège > Département de chimie (sciences) > CITOS
Melnyk, Oleg 
 These authors have contributed equally to this work.
Language :
English
Title :
Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides
Publication date :
2018
Journal title :
Nature Communications
eISSN :
2041-1723
Publisher :
Nature Publishing Group, United Kingdom
Volume :
9
Pages :
2847
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 23 July 2018

Statistics


Number of views
216 (26 by ULiège)
Number of downloads
82 (3 by ULiège)

Scopus citations®
 
32
Scopus citations®
without self-citations
26
OpenCitations
 
34

Bibliography


Similar publications



Contact ORBi