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.

ChemInform Abstract: Head-to-Tail Cyclic Peptides and Cyclic Peptide Libraries

ChemInform ◽  
2000 ◽  
Vol 31 (47) ◽  
pp. no-no
Author(s):  
Arno F. Spatola ◽  
Peteris Romanovskis
Keyword(s):  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Peptide Libraries

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 Methods for the Creation of Cyclic Peptide Libraries for Use in Lead Discovery

2015 ◽  
Vol 20 (5) ◽  
pp. 563-576 ◽  
Author(s):  
Andrew D. Foster ◽  
James D. Ingram ◽  
Eilidh K. Leitch ◽  
Katherine R. Lennard ◽  
Eliot L. Osher ◽  
...  
Keyword(s):  
Protein Interactions ◽  
High Throughput Screening ◽  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Peptide Libraries ◽  
Successful Implementation ◽  
Protein Protein Interactions ◽  
Lead Discovery ◽  
Small Molecule Libraries ◽  
The Creation

The identification of initial hits is a crucial stage in the drug discovery process. Although many projects adopt high-throughput screening of small-molecule libraries at this stage, there is significant potential for screening libraries of macromolecules created using chemical biology approaches. Not only can the production of the library be directly interfaced with a cell-based assay, but these libraries also require significantly fewer resources to generate and maintain. In this context, cyclic peptides are increasingly viewed as ideal scaffolds and have proven capability against challenging targets such as protein-protein interactions. Here we discuss a range of methods used for the creation of cyclic peptide libraries and detail examples of their successful implementation.

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

On-Resin Native Chemical Ligation for Cyclic Peptide Synthesis1,2

2004 ◽  
Vol 69 (12) ◽  
pp. 4101-4107 ◽  
Author(s):  
Judit Tulla-Puche ◽  
George Barany
Keyword(s):  
Cyclic Peptide ◽  
Native Chemical Ligation ◽  
Chemical Ligation

scholarly journals Virtual Screening Using Combinatorial Cyclic Peptide Libraries Reveals Protein Interfaces Readily Targetable by Cyclic Peptides

2015 ◽  
Vol 55 (3) ◽  
pp. 600-613 ◽  
Author(s):  
Fergal J. Duffy ◽  
Darragh O’Donovan ◽  
Marc Devocelle ◽  
Niamh Moran ◽  
David J. O’Connell ◽  
...  
Keyword(s):  
Virtual Screening ◽  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Peptide Libraries ◽  
Protein Interfaces

Efficient Synthesis of Protein Mimics by Sequential Native Chemical Ligation

2014 ◽  
Vol 16 (8) ◽  
pp. 2138-2141 ◽  
Author(s):  
Helmus van de Langemheen ◽  
H. (Linda) C. Quarles van Ufford ◽  
John A. W. Kruijtzer ◽  
Rob M. J. Liskamp
Keyword(s):  
Native Chemical Ligation ◽  
Efficient Synthesis ◽  
Chemical Ligation ◽  
Protein Mimics

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.

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