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

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.

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.

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

Scaffolded multiple cyclic peptide libraries for protein mimics by native chemical ligation

2014 ◽  
Vol 12 (25) ◽  
pp. 4471-4478 ◽  
Author(s):  
H. van de Langemheen ◽  
M. van Hoeke ◽  
H. C. Quarles van Ufford ◽  
J. A. W. Kruijtzer ◽  
R. M. J. Liskamp
Keyword(s):  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Peptide Libraries ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Protein Mimics

The accessibility to collections, libraries and arrays of cyclic peptides is increasingly important since cyclic peptides may provide better mimics of the loop-like structures ubiquitously present in and – especially – on the surface of proteins.

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.

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

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.

scholarly journals Autocatalytic and oscillatory reaction networks that form guanidines and products of their cyclization

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Alexander I. Novichkov ◽  
Anton I. Hanopolskyi ◽  
Xiaoming Miao ◽  
Linda J. W. Shimon ◽  
Yael Diskin-Posner ◽  
...  
Keyword(s):  
Chemical Cues ◽  
Native Chemical Ligation ◽  
Reaction Networks ◽  
Oscillatory Reaction ◽  
Experimental Conditions ◽  
Chemical Ligation ◽  
Chemical Systems ◽  
Life On Earth ◽  
Emergence Of Life ◽  
Equilibrium Chemical

AbstractAutocatalytic and oscillatory networks of organic reactions are important for designing life-inspired materials and for better understanding the emergence of life on Earth; however, the diversity of the chemistries of these reactions is limited. In this work, we present the thiol-assisted formation of guanidines, which has a mechanism analogous to that of native chemical ligation. Using this reaction, we designed autocatalytic and oscillatory reaction networks that form substituted guanidines from thiouronium salts. The thiouronium salt-based oscillator show good stability of oscillations within a broad range of experimental conditions. By using nitrile-containing starting materials, we constructed an oscillator where the concentration of a bicyclic derivative of dihydropyrimidine oscillates. Moreover, the mixed thioester and thiouronium salt-based oscillator show unique responsiveness to chemical cues. The reactions developed in this work expand our toolbox for designing out-of-equilibrium chemical systems and link autocatalytic and oscillatory chemistry to the synthesis of guanidinium derivatives and the products of their transformations including analogs of nucleobases.

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