One-pot native chemical ligation by combination of two orthogonal thioester precursors

2017 ◽  
Vol 53 (13) ◽  
pp. 2114-2117 ◽  
Author(s):  
Yuya Asahina ◽  
Toru Kawakami ◽  
Hironobu Hojo
Keyword(s):  
Native Chemical Ligation ◽  
Protecting Group ◽  
One Pot ◽  
Chemical Ligation ◽  
Ligation Reaction ◽  
Ligation Method ◽  
Peptide Ligation

We developed a one-pot peptide ligation method using two orthogonal thioester precursors and a protecting group for the ligation reaction between Asp and Cys.

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.

21.11.7 Chemoselective Ligation Methods Based on the Concept of Native Chemical Ligation

2021 ◽  
Author(s):  
L. R. Malins ◽  
R. J. Payne
Keyword(s):  
Peptide Synthesis ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Chemoselective Ligation ◽  
Ligation Reaction ◽  
Recent Developments ◽  
Peptide Ligation

AbstractThis chapter extends from the earlier Science of Synthesis contribution on peptide synthesis (Section 21.11) and focuses on recent developments in chemoselective ligation chemistry based on the logic of native chemical ligation. Synthetic strategies that broaden the scope and versatility of the ligation reaction and that have been widely adopted for the preparation of homogeneous peptides and proteins are highlighted. Methods enabling the efficient preparation of peptide ligation precursors are also included in this chapter.

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.

scholarly journals Rapid One-Pot Iterative Diselenide-Selenoester Ligation using a Novel Coumarin-Based Photolabile Protecting Group

2021 ◽  
Author(s):  
Lucas Kambanis ◽  
Timothy S Chisholm ◽  
Sameer Kulkarni ◽  
Richard James Payne
Keyword(s):  
Protecting Group ◽  
One Pot ◽  
Ligation Reaction ◽  
Photolabile Protecting Group ◽  
Peptide Ligation

The development of an iterative one-pot peptide ligation strategy is described that capitalises on the rapid and efficient nature of the diselenide-selenoester ligation reaction, together with photodeselenisation chemistry. This ligation...

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.

scholarly journals A synthetic approach to ‘click’ neoglycoprotein analogues of EPO employing one-pot native chemical ligation and CuAAC chemistry

2019 ◽  
Vol 10 (3) ◽  
pp. 815-828 ◽  
Author(s):  
D. J. Lee ◽  
A. J. Cameron ◽  
T. H. Wright ◽  
P. W. R. Harris ◽  
M. A. Brimble
Keyword(s):  
Native Chemical Ligation ◽  
Synthetic Approach ◽  
One Pot ◽  
Chemical Ligation ◽  
Synthetic Methodologies

The batch-wise variability of commercial erythropoietin (EPO) preparations warrants development of more advanced synthetic methodologies. We have developed a diverse chemical toolkit to prepare ‘click’ neoglycoprotein variants of EPO.

One-Pot/Sequential Native Chemical Ligation Using Photocaged Crypto-thioester

2016 ◽  
Vol 18 (3) ◽  
pp. 596-599 ◽  
Author(s):  
Keisuke Aihara ◽  
Kosuke Yamaoka ◽  
Naoto Naruse ◽  
Tsubasa Inokuma ◽  
Akira Shigenaga ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation

Singlet oxygen-mediated one-pot chemoselective peptide–peptide ligation

2017 ◽  
Vol 15 (38) ◽  
pp. 8140-8144 ◽  
Author(s):  
Eirini Antonatou ◽  
Yentl Verleysen ◽  
Annemieke Madder
Keyword(s):  
Singlet Oxygen ◽  
One Pot ◽  
Specific Chemical ◽  
Chemical Ligation ◽  
Site Specific ◽  
Peptide Segments ◽  
Peptide Ligation

We here describe a furan oxidation based site-specific chemical ligation approach using unprotected peptide segments.

Rapid Access to ω-Conotoxin Chimeras using Native Chemical Ligation

2009 ◽  
Vol 62 (10) ◽  
pp. 1333 ◽  
Author(s):  
Gene Hopping ◽  
Richard J. Lewis ◽  
Paul F. Alewood
Keyword(s):  
Ligand Binding ◽  
Coupling Efficiency ◽  
Native Chemical Ligation ◽  
Binding Assays ◽  
Chemical Ligation ◽  
Receptor Recognition ◽  
Single Protein ◽  
Difficult Sequences ◽  
Peptide Segments ◽  
Ligation Method

Grafting different regions of related peptides together to form a single protein chimera is a valuable tool in rapidly elucidating regions of activity or selectivity in peptides and proteins. To conveniently evaluate the contributions of the N- and C-terminal segments of ω-conotoxins CVID and MVIIC to activity, we employed native chemical ligation in CVID-MVIIC chimera design. Assembly of these peptide segments via the ligation method improved overall yield and coupling efficiency, with no difficult sequences encountered in contrast to the traditional full-length chain assembly of CVID. Radio-ligand binding assays revealed regions of importance for receptor recognition.

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