Peptide Thioester Formation via an Intramolecular N to S Acyl Shift for Peptide Ligation

2014 ◽  
pp. 107-135 ◽  
Author(s):  
Toru Kawakami
Keyword(s):  
Peptide Thioester ◽  
Peptide Ligation

Facilitating Subtiligase-Catalyzed Peptide Ligation Reactions by Using Peptide Thioester Substrates

2018 ◽  
Vol 20 (21) ◽  
pp. 6691-6694 ◽  
Author(s):  
Xiaohong Tan ◽  
Renliang Yang ◽  
Chuan-Fa Liu
Keyword(s):  
Peptide Thioester ◽  
Peptide Ligation

scholarly journals Construction of diverse peptide structural architectures via chemoselective peptide ligation

2021 ◽  
Author(s):  
Carina Hey Pui Cheung ◽  
Jianchao Xu ◽  
Chi Lung Lee ◽  
Yanfeng Zhang ◽  
Ruohan Wei ◽  
...  
Keyword(s):  
Synthetic Strategy ◽  
Peptide Ligation

Herein, we report the development of a facile synthetic strategy for constructing diverse peptide structural architectures via chemoselective peptide ligation. The key advancement involved is to utilize the benzofuran moiety...

Preparation of Peptide o-Aminoanilides Using a Modified Dawson's Linker for Microwave-Assisted Peptide Synthesis

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1956-1960 ◽  
Author(s):  
Shugo Tsuda ◽  
Taku Yoshiya ◽  
Tsuyoshi Uemura ◽  
Masayoshi Mochizuki ◽  
Hideki Nishio
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Side Reactions ◽  
Microwave Assisted Synthesis ◽  
Terminal Amino Acid ◽  
Nitrobenzoic Acid ◽  
Microwave Assisted ◽  
Peptide Thioester ◽  
Terminal Amino

Based on the structure of Dawson’s 3,4-diaminobenzoic acid (Dbz) linker designed for Fmoc solid-phase peptide-thioester synthesis, the 4-amino-3-nitrobenzoic acid [Dbz(NO2)] linker was developed for microwave-assisted synthesis. The Dbz(NO2) linker can be readily converted into the Dbz linker by on-resin reduction with SnCl2 after construction of the protected peptide resin. Although epimerization of C-terminal amino acid restricts the use of Dbz(NO2) linker to the synthesis of peptide-Gly-thioester, use of this linker can prevent side reactions that arise when Dbz or Dbz(Aloc) linkers are used in the microwave-assisted synthesis of Gly-rich peptides.

A novel post-ligation thioesterification device enables peptide ligation in the N to C direction: synthetic study of human glycodelin

2013 ◽  
Vol 20 (1) ◽  
pp. 55-61 ◽  
Author(s):  
Takaomi Takenouchi ◽  
Hidekazu Katayama ◽  
Yuko Nakahara ◽  
Yoshiaki Nakahara ◽  
Hironobu Hojo
Keyword(s):  
Peptide Ligation

scholarly journals Catalysis of Hydrazone and Oxime Peptide Ligation by Arginine

2020 ◽  
Author(s):  
Nathalie Ollivier ◽  
Vangelis Agouridas ◽  
Benoît Snella ◽  
Rémi Desmet ◽  
Hervé Drobecq ◽  
...  
Keyword(s):  
Protein Aggregation ◽  
Phosphate Buffer ◽  
Side Chain ◽  
Neutral Ph ◽  
Arginine Hydrochloride ◽  
Guanidinium Group ◽  
Aggregation Inhibitor ◽  
Peptide Ligation

Hydrazone and oxime peptide ligations are catalyzed by arginine. The catalysis is assisted intramolecularly by the side-chain guanidinium group. Hydrazone ligation in the presence of arginine proceeds efficiently in phosphate buffer at neutral pH but is particularly powerful in bicarbonate/CO<sub>2</sub> buffer. In addition to acting as a catalyst, arginine prevents the aggregation of proteins during ligation. With its dual properties as nucleophilic catalyst and protein aggregation inhibitor, arginine hydrochloride is a useful addition to the hydrazone/oxime ligation toolbox.<br>

Peptide Ligation by a Reversible and Reusable C-Terminal Thiol Handle

2005 ◽  
Vol 7 (22) ◽  
pp. 5003-5006 ◽  
Author(s):  
Yi-An Lu ◽  
James P. Tam
Keyword(s):  
Peptide Ligation

Synthesis of Histidine-Containing Oligopeptides via Histidine-Promoted Peptide Ligation

2018 ◽  
Vol 13 (4) ◽  
pp. 400-403 ◽  
Author(s):  
Kai-Jin Huang ◽  
Yi-Chen Huang ◽  
Yuya A. Lin
Keyword(s):  
Peptide Ligation
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