Literature DB >> 26948900

Macrocyclization of Unprotected Peptide Isocyanates.

Alexander A Vinogradov1, Zi-Ning Choo1, Kyle A Totaro1, Bradley L Pentelute1.   

Abstract

A chemistry for the facile two-component macrocyclization of unprotected peptide isocyanates is described. Starting from peptides containing two glutamic acid γ-hydrazide residues, isocyanates can be readily accessed and cyclized with hydrazides of dicarboxylic acids. The choice of a nucleophilic linker allows for the facile modulation of biochemical properties of a macrocyclic peptide. Four cyclic NYAD-1 analogues were synthesized using the described method and displayed a range of biological activities.

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Year:  2016        PMID： 26948900     DOI： 10.1021/acs.orglett.5b03626

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  In-solution enrichment identifies peptide inhibitors of protein-protein interactions.

Authors:  Fayçal Touti; Zachary P Gates; Anupam Bandyopadhyay; Guillaume Lautrette; Bradley L Pentelute
Journal:  Nat Chem Biol       Date:  2019-03-18       Impact factor: 15.040

2.  Adapting the Glaser Reaction for Bioconjugation: Robust Access to Structurally Simple, Rigid Linkers.

Authors:  Anthony P Silvestri; Philip A Cistrone; Philip E Dawson
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-21       Impact factor: 15.336

Review 3.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876

Review 4.  Visualizing HIV-1 Capsid and Its Interactions with Antivirals and Host Factors.

Authors:  Morganne Wilbourne; Peijun Zhang
Journal:  Viruses       Date:  2021-02-04       Impact factor: 5.818

5.  Divergent unprotected peptide macrocyclisation by palladium-mediated cysteine arylation.

Authors:  Anthony J Rojas; Chi Zhang; Ekaterina V Vinogradova; Nathan H Buchwald; John Reilly; Bradley L Pentelute; Stephen L Buchwald
Journal:  Chem Sci       Date:  2017-03-24       Impact factor: 9.825

6.  Stereoisomerism of stapled peptide inhibitors of the p53-Mdm2 interaction: an assessment of synthetic strategies and activity profiles.

Authors:  Tsz Ying Yuen; Christopher J Brown; Yuezhen Xue; Yaw Sing Tan; Fernando J Ferrer Gago; Xue Er Lee; Jin Yong Neo; Dawn Thean; Hung Yi Kristal Kaan; Anthony W Partridge; Chandra S Verma; David P Lane; Charles W Johannes
Journal:  Chem Sci       Date:  2019-05-30       Impact factor: 9.825
  6 in total

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