Literature DB >> 28470238

The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems.

Diana Gimenez1, Caitlin A Mooney, Anica Dose, Graham Sandford, Christopher R Coxon, Steven L Cobb.   

Abstract

The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing SNAr arylation reactions in the presence of a range of nucleophilic peptide side chains (i.e. cysteine, tyrosine, serine and lysine) under mild conditions. Moreover, we have shown how one-step peptide-modification using perfluoroheteroaromatics can deliver enhanced proteolytic stability in pharmaceutically-relevant peptides such as oxytocin.

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Year:  2017        PMID： 28470238     DOI： 10.1039/c7ob00283a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  10 in total

Review 1.  Arylation Chemistry for Bioconjugation.

Authors:  Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

Review 2.  Small, but powerful and attractive: 19F in biomolecular NMR.

Authors:  Angela M Gronenborn
Journal:  Structure       Date:  2021-12-13       Impact factor: 5.006

Review 3.  Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

Authors:  William D G Brittain; Christopher R Coxon
Journal:  Chemistry       Date:  2021-12-02       Impact factor: 5.020

4.  Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions.

Authors:  William D G Brittain; Steven L Cobb
Journal:  Org Biomol Chem       Date:  2019-02-20       Impact factor: 3.876

5.  Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl-perfluoro-pyridines.

Authors:  Andrew J Peloquin; Cynthia A Corley; Sonya K Adas; Gary J Balaich; Scott T Iacono
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-07-04

6.  Fluoromaticity: The Molecular Orbital Contributions of Fluorine Substituents to the π-Systems of Aromatic Rings.

Authors:  Timothy J Fuhrer; Matthew Houck; Scott T Iacono
Journal:  ACS Omega       Date:  2021-11-23

Review 7.  Perfluoropyridine: Discovery, Chemistry, and Applications in Polymers and Material Science.

Authors:  Ritesh Gautam; Ian Geniza; Scott T Iacono; Chadron M Friesen; Abby R Jennings
Journal:  Molecules       Date:  2022-02-28       Impact factor: 4.411

8.  New Molecular Insights into the Inhibition of Dipeptidyl Peptidase-4 by Natural Cyclic Peptide Oxytocin.

Authors:  Veera C S R Chittepu; Poonam Kalhotra; Tzayhri Osorio-Gallardo; Cristian Jiménez-Martínez; Raúl René Robles-de la Torre; Tzayhri Gallardo-Velazquez; Guillermo Osorio-Revilla
Journal:  Molecules       Date:  2019-10-28       Impact factor: 4.411

Review 9.  Synthesis of complex unnatural fluorine-containing amino acids.

Authors:  William D G Brittain; Carissa M Lloyd; Steven L Cobb
Journal:  J Fluor Chem       Date:  2020-11       Impact factor: 2.050

10.  Theoretical Prediction and Explanation of Reaction Site Selectivity in the Addition of a Phenoxy Group to Perfluoropyrimidine, Perfluoropyridazine, and Perfluoropyrazine.

Authors:  Timothy J Fuhrer; Matthew Houck; Rachel M Chapman; Scott T Iacono
Journal:  Molecules       Date:  2021-12-16       Impact factor: 4.411
  10 in total

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