Journal ArticleDOI
Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: potential for library synthesis.
TLDR
It is demonstrated that properly controlled palladium-mediated deprotection of Allyl/Alloc protecting groups can be used to prepare cyclic peptides on the resin using an automated peptide synthesizer and cyclic glucagon analogue containing 24 amino acid residues.Abstract:
Automated and manual deprotection methods for allyl/allyloxycarbonyl (Allyl/Alloc) were evaluated for the preparation of side-chain-to-side-chain cyclic peptides. Using a standard Allyl/Alloc deprotection method, a small library of cyclic peptides with lactam bridges (with seven amino acids) was prepared on an automatic peptide synthesizer. We demonstrate that the Guibe method for removing Allyl/Alloc protecting groups under specific neutral conditions [Pd(PPh3)4/PhSiH3)/DCM] can be a useful, efficient and reliable method for preparing long cyclic peptides on a resin. We have also manually synthesized a cyclic glucagon analogue containing 24 amino acid residues. These results demonstrated that properly controlled palladium-mediated deprotection of Allyl/Alloc protecting groups can be used to prepare cyclic peptides on the resin using an automated peptide synthesizer and cyclic peptides with a long chain.read more
Citations
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Journal ArticleDOI
The cyclization of peptides and depsipeptides
TL;DR: Developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides are highlighted.
Journal ArticleDOI
Synthesis and conformational analysis of a cyclic peptide obtained via i to i+4 intramolecular side-chain to side-chain azide-alkyne 1,3-dipolar cycloaddition.
Sonia Cantel,Alexandra Le Chevalier Isaad,Mario Scrima,Jay J. Levy,Richard D. DiMarchi,Paolo Rovero,Jose A. Halperin,Anna Maria D'Ursi,Anna Maria Papini,Michael Chorev +9 more
TL;DR: The employment of Cu(I)-catalyzed 1,3-dipolar cycloaddition of side chains modified with azido and alkynyl functions is reported and alternative synthetic routes to efficiently generate 1,4-disubstituted [1,2,3]triazolyl-containing cyclopeptides are explored.
Journal ArticleDOI
The synthesis and study of side‐chain lactam‐bridged peptides
TL;DR: Defining the functional roles of the amphiphilic alpha-helices in medium-sized peptide hormones, and studying helix propagation from rigid, alpha-helix initiating bicyclic peptides are among the most exciting developments currently underway in this field.
Journal ArticleDOI
Palladium-catalysed reactions in solid phase organic synthesis
Journal ArticleDOI
Accelerated chromatin biochemistry using DNA-barcoded nucleosome libraries
Uyen T. T. Nguyen,Lenka Bittova,Manuel M. Müller,Beat Fierz,Yael David,Brian Houck-Loomis,Vanessa Feng,Geoffrey P. Dann,Tom W. Muir +8 more
TL;DR: This ultrasensitive workflow allowed us to collect thousands of biochemical data points revealing the binding preferences of various nuclear factors for PTM patterns and how preexisting PTMs, alone or synergistically, affect further PTM deposition via cross-talk mechanisms.
References
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Journal ArticleDOI
Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)]
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Potent and prolonged acting cyclic lactam analogues of alpha-melanotropin: design based on molecular dynamics.
Fahad Al-Obeidi,Ana Maria de Lauro Castrucci,Ana Maria de Lauro Castrucci,Mac E. Hadley,Victor J. Hruby +4 more
TL;DR: New insights are provided into the structural and conformational requirements of alpha-MSH and its analogues at two different types of pigment cell (melanocyte) receptors.
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A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides
Steven A. Kates,Nuria A. Solé,Charles R. Johnson,Derek Hudson,George Barany,Fernando Albericio +5 more
TL;DR: In this article, head-to-tail cyclic peptides are made by an efficient three-dimensional orthogonal solid phase strategy (Fmoc/tBu/allyl), featuring side-chain anchoring to PAC or PAL supports, selective palladium (O)-catalyzed allyl removal, and resin-bound cyclization mediated by BOP/HOBt/DIEA.
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Allylic protecting groups and their use in a complex environment part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology
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