An efficient solid-phase synthesis of peptidyl-N-acetylguanidines for use in native chemical ligation

2016 ◽  
Vol 22 (5) ◽  
pp. 343-351 ◽  
Author(s):  
Ryo Okamoto ◽  
Madoka Isoe ◽  
Masayuki Izumi ◽  
Yasuhiro Kajihara
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Phase Synthesis

scholarly journals The Problem of Aspartimide Formation During Protein Chemical Synthesis Using SEA-Mediated Ligation

2019 ◽  
Author(s):  
Jennifer Bouchenna ◽  
Magalie Sénéchal ◽  
Hervé Drobecq ◽  
Jérôme Vicogne ◽  
Oleg Melnyk
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Reaction ◽  
Peptide Bond ◽  
Protein Targets ◽  
Chemical Ligation ◽  
Phase Synthesis ◽  
Bond Forming ◽  
Aspartimide Formation ◽  
Peptide Segments

Aspartimide formation often complicates the solid phase synthesis of peptides. Much less discussed is the potential occurrence of this side-reaction during the coupling of peptide segments using chemoselective peptide bond forming reactions such as the native chemical ligation and extended methods. Here we describe how to manage this problem using bis(2-sulfenylethyl)amido (SEA)-mediated ligation and SUMO-2/SUMO-3 as protein targets.<br>

scholarly journals The Problem of Aspartimide Formation During Protein Chemical Synthesis Using SEA-Mediated Ligation

2019 ◽  
Author(s):  
Jennifer Bouchenna ◽  
Magalie Sénéchal ◽  
Hervé Drobecq ◽  
Jérôme Vicogne ◽  
Oleg Melnyk
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Reaction ◽  
Peptide Bond ◽  
Protein Targets ◽  
Chemical Ligation ◽  
Phase Synthesis ◽  
Bond Forming ◽  
Aspartimide Formation ◽  
Peptide Segments

Aspartimide formation often complicates the solid phase synthesis of peptides. Much less discussed is the potential occurrence of this side-reaction during the coupling of peptide segments using chemoselective peptide bond forming reactions such as the native chemical ligation and extended methods. Here we describe how to manage this problem using bis(2-sulfenylethyl)amido (SEA)-mediated ligation and SUMO-2/SUMO-3 as protein targets.<br>

scholarly journals A new method of N to C sequential ligation using thioacid capture ligation and native chemical ligation

2018 ◽  
Vol 5 (6) ◽  
pp. 172455 ◽  
Author(s):  
Wen Hou ◽  
Lei Liu ◽  
Xiaohong Zhang ◽  
Chuanfa Liu
Keyword(s):  
Solid Phase ◽  
Native Chemical Ligation ◽  
Large Protein ◽  
Chemical Ligation ◽  
Phase Synthesis ◽  
Protein Size ◽  
Sweet Protein ◽  
Combined Use ◽  
One Step ◽  
Peptide Ligation

Sequential peptide ligation strategy becomes more and more important in large protein or long peptides chemical synthesis due to the limited peptide/protein size obtained by solid phase synthesis of individual peptides or even one-step peptide ligation. Herein, we developed an alternative method which could perform the sequential peptide ligation of several segments from N to C direction based on the combined use of thioacid capture ligation and native chemical ligation. The sweet protein monellin was produced through this strategy on a scale of multi-milligrams.

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