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.

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 Reinvestigation of a Critical Reductive Amination Step Leads to an Optimized Protocol for the Synthesis of N-2-Hydroxybenzylcysteine Peptide Crypto-Thioesters

2020 ◽  
Author(s):  
Skander Abboud ◽  
Vincent AUCAGNE
Keyword(s):  
Peptide Synthesis ◽  
Reaction Mechanisms ◽  
Reductive Amination ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Optimized Protocol ◽  
Depth Study

An in-depth study of the Fmoc-based solid phase peptide synthesis of N-Hnb-Cys crypto-thioester peptides, advantageous building blocks for the native chemical ligation-based synthesis of proteins, led to the identification of epimerized and imidazolidinone side products formed during a key reductive amination step. The understanding of the underlying reaction mechanisms was crucial for the developement of an automatable optimized synthetic protocol.

scholarly journals Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation

2017 ◽  
Vol 8 (1) ◽  
pp. 117-123 ◽  
Author(s):  
Hader E. Elashal ◽  
Yonnette E. Sim ◽  
Monika Raj
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solid Support ◽  
Native Chemical Ligation ◽  
Selective Activation ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

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 Thiazolidine Deprotection by 2-Aminobenzamide-Based Aldehyde Scavenger for One-Pot Multiple Peptide Ligation

2021 ◽  
Author(s):  
Koki Nakatsu ◽  
Hitoshi Murakami ◽  
Gosuke Hayashi ◽  
Akimitsu Okamoto
Keyword(s):  
Native Chemical Ligation ◽  
High Yield ◽  
Side Reactions ◽  
Model Peptide ◽  
One Pot ◽  
Chemical Ligation ◽  
Good Ability ◽  
Synthetic Proteins ◽  
Short Time ◽  
Peptide Ligation

Strategies for one-pot peptide ligation enable chemists to access synthetic proteins at a high yield in a short time. Herein, we report a new one-pot multi-segments ligation strategy using N-terminal thiazolidine (Thz) peptide and a formaldehyde scavenger. Among our designed 2-aminobenzamide-based aldehyde scavengers, 2-amino-5-methoxy-N’,N’-dimethylbenzohydrazide showed a good ability to capture formaldehyde from Thz at pH 4.0. This scavenger had compatibility with the conditions of native chemical ligation at pH 7.5. Using this scavenger for a model peptide ligation system, we performed one-pot four-segment ligation at a high yield without significant side reactions.

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