Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

2017 ◽  
Vol 15 (2) ◽  
pp. 316-319 ◽  
Author(s):  
Victor P. Terrier ◽  
Agnès F. Delmas ◽  
Vincent Aucagne
Keyword(s):  
Cyclic Peptides ◽  
Native Chemical Ligation ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Chemical Ligation

We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides. It is based on the intramolecular native chemical ligation of thioesters generated in situ from N-Hnb-Cys crypto-thioesters. The strategy is applied to a representative range of natural cyclic disulfide-rich peptide sequences.

A route to cyclic peptides and glycopeptides by native chemical ligation using in situ derived thioesters

2006 ◽  
Vol 47 (12) ◽  
pp. 1969-1972 ◽  
Author(s):  
Jiehao Chen ◽  
J. David Warren ◽  
Bin Wu ◽  
Gong Chen ◽  
Qian Wan ◽  
...  
Keyword(s):  
Cyclic Peptides ◽  
Native Chemical Ligation ◽  
Chemical Ligation

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.

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

scholarly journals In Situ Vesicle Formation by Native Chemical Ligation

2014 ◽  
Vol 53 (51) ◽  
pp. 14102-14105 ◽  
Author(s):  
Roberto J. Brea ◽  
Christian M. Cole ◽  
Neal K. Devaraj
Keyword(s):  
Native Chemical Ligation ◽  
Vesicle Formation ◽  
Chemical Ligation

scholarly journals Making Ends Meet: Microwave-Accelerated Synthesis of Cyclic and Disulfide Rich Proteins Via In Situ Thioesterification and Native Chemical Ligation

2012 ◽  
Vol 19 (1) ◽  
pp. 43-54 ◽  
Author(s):  
Sunithi Gunasekera ◽  
Teshome L. Aboye ◽  
Walid A. Madian ◽  
Hesham R. El-Seedi ◽  
Ulf Göransson
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation

scholarly journals Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1923-1928 ◽  
Author(s):  
Derek Macmillan ◽  
Durbis Castillo-Pazos
Keyword(s):  
Glutamic Acid ◽  
Chain Length ◽  
Cyclic Peptides ◽  
Fine Tuning ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Popular Method ◽  
Slow Reaction

N→S Acyl transfer is a popular method for the postsynthesis production of peptide C α-thioesters for use in native chemical ligation and for the synthesis of head-to-tail cyclic peptides. Meanwhile thioester formation at the side chain of aspartic or glutamic acids, leading to tail-to-side-chain-cyclized species, is less common. Herein we explore the potential for cysteine to function as a latent thioester when appended to the side chain of glutamic acid. Initial insights gained through study of C-terminal β-alanine as a model for the increased chain length were ultimately applied to peptide macrocyclization. Our results emphasize the increased barrier to acyl transfer at the glutamic acid side chain and indicate how a slow reaction, facilitated by cysteine itself, may be accelerated by fine-tuning of the stereoelectronic environment.

Efficient synthesis of longer Aβ peptides via removable backbone modification

2016 ◽  
Vol 14 (22) ◽  
pp. 5012-5018 ◽  
Author(s):  
Chao Zuo ◽  
Shan Tang ◽  
Yan-Yan Si ◽  
Zhipeng A. Wang ◽  
Chang-Lin Tian ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
New Method ◽  
Native Chemical Ligation ◽  
Efficient Synthesis ◽  
Chemical Ligation ◽  
Aβ Peptides ◽  
Backbone Modification

This paper describes a new method for the efficient chemical synthesis of longer Aβ peptides with the combination of the RBM strategy and native chemical ligation.

Native Chemical Ligation through in Situ O to S Acyl Shift

2004 ◽  
Vol 6 (26) ◽  
pp. 4861-4864 ◽  
Author(s):  
Paolo Botti ◽  
Matteo Villain ◽  
Sonia Manganiello ◽  
Hubert Gaertner
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation

scholarly journals Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides

2018 ◽  
Vol 9 (1) ◽  
Author(s):  
Nathalie Ollivier ◽  
Thomas Toupy ◽  
Ruben C. Hartkoorn ◽  
Rémi Desmet ◽  
Jean-Christophe M. Monbaliu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Cyclic Peptides ◽  
Native Chemical Ligation ◽  
Chemical Ligation
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