scholarly journals A straightforward methodology to overcome solubility challenges for N-terminal cysteinyl peptide segments used in native chemical ligation

2021 ◽  
Author(s):  
Skander A. Abboud ◽  
El hadji Cisse ◽  
Michel Doudeau ◽  
Hélène Bénédetti ◽  
Vincent Aucagne
Keyword(s):  
Chemical Synthesis ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Segments ◽  
Straightforward Approach

We herein describe a straightforward approach for the introduction of a solubilizing tag on N-terminal cysteinyl segments used in native chemical ligation-based protein chemical synthesis. Conveniently, the tag is removed during the ligation.

scholarly journals A Straightforward Methodology to Overcome Solubility Challenges for N-Terminal Cysteinyl Peptide Segments Used in Native Chemical Ligation

2020 ◽  
Author(s):  
Skander Abboud ◽  
El hadji Cisse ◽  
Michel Doudeau ◽  
Hélène Bénédetti ◽  
Vincent AUCAGNE
Keyword(s):  
Amino Acids ◽  
Chemical Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
Chemical Ligation ◽  
Limited Solubility ◽  
Peptide Segments

One of the main limitations encountered during the chemical synthesis of proteins through native chemical ligation (NCL) is the limited solubility of some of the peptide segments. The most commonly used solution to overcome this problem is to derivatize the segment with a temporary solubilizing tag. Conveniently, the tag can be introduced on the thioester segment in such a way that it is removed concomitantly with the NCL reaction. We herein describe a generalization of this approach to N-terminal cysteinyl segment counterparts, using a straightforward synthetic approach that can be easily automated from commercially available building blocks, and applied it to a well-known problematic target, SUMO-2 (93 amino acids).

scholarly journals A Straightforward Methodology to Overcome Solubility Challenges for N-Terminal Cysteinyl Peptide Segments Used in Native Chemical Ligation

2020 ◽  
Author(s):  
Skander Abboud ◽  
El hadji Cisse ◽  
Michel Doudeau ◽  
Hélène Bénédetti ◽  
Vincent AUCAGNE
Keyword(s):  
Amino Acids ◽  
Chemical Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
Chemical Ligation ◽  
Limited Solubility ◽  
Peptide Segments

One of the main limitations encountered during the chemical synthesis of proteins through native chemical ligation (NCL) is the limited solubility of some of the peptide segments. The most commonly used solution to overcome this problem is to derivatize the segment with a temporary solubilizing tag. Conveniently, the tag can be introduced on the thioester segment in such a way that it is removed concomitantly with the NCL reaction. We herein describe a generalization of this approach to N-terminal cysteinyl segment counterparts, using a straightforward synthetic approach that can be easily automated from commercially available building blocks, and applied it to a well-known problematic target, SUMO-2 (93 amino acids).

One-pot hydrazide-based native chemical ligation for efficient chemical synthesis and structure determination of toxin Mambalgin-1

2014 ◽  
Vol 50 (44) ◽  
pp. 5837-5839 ◽  
Author(s):  
Man Pan ◽  
Yao He ◽  
Ming Wen ◽  
Fangming Wu ◽  
Demeng Sun ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Snake Venom ◽  
Structure Determination ◽  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation ◽  
Venom Toxin ◽  
Snake Venom Toxin ◽  
Switch Strategy

An efficient one-pot chemical synthesis of snake venom toxin Mambalgin-1 was achieved using an azide-switch strategy combined with hydrazide-based native chemical ligation.

Facile and efficient chemical synthesis of APET×2, an ASIC-targeting toxin, via hydrazide-based native chemical ligation

Tetrahedron ◽  
2015 ◽  
Vol 71 (21) ◽  
pp. 3363-3366
Author(s):  
Si-Jian Li ◽  
Da-Liang Qu ◽  
Ye-Hai Wang ◽  
Yao He ◽  
Min Wen ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Native Chemical Ligation ◽  
Chemical Ligation

Chemical Synthesis of A Pore-Forming Antimicrobial Protein, Caenopore-5, by Using Native Chemical Ligation at a Glu-Cys Site

ChemBioChem ◽  
2014 ◽  
Vol 16 (2) ◽  
pp. 328-336 ◽  
Author(s):  
Karima Medini ◽  
Paul W. R. Harris ◽  
Kiel Hards ◽  
Andrew J. Dingley ◽  
Gregory M. Cook ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Native Chemical Ligation ◽  
Antimicrobial Protein ◽  
Chemical Ligation

scholarly journals Total chemical synthesis of human interferon alpha-2b via native chemical ligation

2015 ◽  
Vol 21 (7) ◽  
pp. 554-560 ◽  
Author(s):  
Jing Li ◽  
Clara Lehmann ◽  
Xishan Chen ◽  
Fabio Romerio ◽  
Wuyuan Lu
Keyword(s):  
Chemical Synthesis ◽  
Interferon Alpha ◽  
Native Chemical Ligation ◽  
Human Interferon ◽  
Chemical Ligation ◽  
Interferon Alpha 2B

scholarly journals Chemical synthesis of proteins using hydrazide intermediates

2015 ◽  
Vol 3 (1) ◽  
pp. 107-116 ◽  
Author(s):  
Yi-Chao Huang ◽  
Ge-Min Fang ◽  
Lei Liu
Keyword(s):  
Protein Synthesis ◽  
Chemical Synthesis ◽  
Native Chemical Ligation ◽  
Synthesis Methods ◽  
Chemical Transformations ◽  
Chemical Ligation

Abstract Protein chemical synthesis offers useful and otherwise-difficulty-to-obtain biomacromolecules for biological and pharmaceutical studies. Recently, the hydrazide chemistry has drawn attentions in this field as peptide or protein hydrazides can be used as key intermediates for different synthesis and modification purposes. Besides being a traditional bioorthogonal chemical handle, a hydrazide group can serve as a readily accessible precursor of a thioester. This strategy significantly improves the efficiency and scope of native chemical ligation for protein chemical synthesis. Here we review the chemical transformations of peptide or protein hydrazides and total/semi/enzymatic protein synthesis methods involving peptide or protein hydrazides. Several examples of protein chemical synthesis using peptide hydrazides as key intermediates are described.

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