Synthesis of selenocysteine-containing cyclic peptides via tandem N-to-S acyl migration and intramolecular selenocysteine-mediated native chemical ligation

2018 ◽  
Vol 54 (83) ◽  
pp. 11737-11740 ◽  
Author(s):  
Shingo Shimodaira ◽  
Toshiki Takei ◽  
Hironobu Hojo ◽  
Michio Iwaoka
Keyword(s):  
Cyclic Peptides ◽  
Acyl Migration ◽  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation

Cyclic selenocysteine-containing peptides were synthesized via one-pot tandem conversion of N-alkylcysteine-containing selenopeptides.

On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation

2020 ◽  
Vol 56 (6) ◽  
pp. 956-959 ◽  
Author(s):  
Gloria Serra ◽  
Laura Posada ◽  
Hironobu Hojo
Keyword(s):  
Cyclic Peptides ◽  
Acyl Migration ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Fmoc Spps

A novel methodology for the synthesis of cyclic peptides by on-resin intramolecular native chemical ligation (NCL) assisted by N-ethylcysteine using Fmoc/SPPS is described.

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.

Synthesis of Cyclic Peptides Containing a Thioester Handle for Native Chemical Ligation

2012 ◽  
Vol 77 (22) ◽  
pp. 10058-10064 ◽  
Author(s):  
Helmus van de Langemheen ◽  
Arwin J. Brouwer ◽  
Johan Kemmink ◽  
John A. W. Kruijtzer ◽  
Rob M. J. Liskamp
Keyword(s):  
Cyclic Peptides ◽  
Native Chemical Ligation ◽  
Chemical Ligation

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

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.

Imidazole-Aided Native Chemical Ligation: Imidazole as a One-Pot Desulfurization-Amenable Non-Thiol-Type Alternative to 4-Mercaptophenylacetic Acid

2016 ◽  
Vol 22 (50) ◽  
pp. 17940-17944 ◽  
Author(s):  
Ken Sakamoto ◽  
Shugo Tsuda ◽  
Masayoshi Mochizuki ◽  
Yukie Nohara ◽  
Hideki Nishio ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation

1,2,4-Triazole-aided native chemical ligation between peptide-N-acyl-N′-methyl-benzimidazolinone and cysteinyl peptide

2017 ◽  
Vol 53 (90) ◽  
pp. 12236-12239 ◽  
Author(s):  
Ken Sakamoto ◽  
Shugo Tsuda ◽  
Hideki Nishio ◽  
Taku Yoshiya
Keyword(s):  
Native Chemical Ligation ◽  
One Pot ◽  
Chemical Ligation

Novel thiol-additive-free NCL using easy-to-prepare peptide-MeNbz and 1,2,4-triazole can be readily combined with one-pot desulfurization and Cys-modification.

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