Jump to main content
Jump to site search

Issue 12, 2018
Previous Article Next Article

Reversible stapling of unprotected peptides via chemoselective methionine bis-alkylation/dealkylation

Author affiliations

Abstract

We have developed a general peptide macrocyclization strategy that involves a facile and chemoselective methionine bis-alkylation/dealkylation process. This method provides a straightforward and easy approach to generate cyclic peptides with tolerances of all amino acids (including Cys), variable loop sizes, and different linkers. The Met bis-alkylation we apply in this strategy yields two additional on-tether positive charges that could assist in the cellular uptake of the peptides. Notably, the bis-alkylated peptide could be reduced to release the original peptide both in vitro and within cellular environments. This strategy provides an intriguing and facile traceless post-peptide-synthesis modification with enhanced cellular uptakes. Peptides constructed with this method could be utilized to zero in on various protein targets or to achieve other goals, such as drug delivery.

Graphical abstract: Reversible stapling of unprotected peptides via chemoselective methionine bis-alkylation/dealkylation

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Nov 2017, accepted on 20 Feb 2018 and first published on 26 Feb 2018


Article type: Edge Article
DOI: 10.1039/C7SC05109C
Citation: Chem. Sci., 2018,9, 3227-3232
  • Open access: Creative Commons BY license
  •   Request permissions

    Reversible stapling of unprotected peptides via chemoselective methionine bis-alkylation/dealkylation

    X. Shi, R. Zhao, Y. Jiang, H. Zhao, Y. Tian, Y. Jiang, J. Li, W. Qin, F. Yin and Z. Li, Chem. Sci., 2018, 9, 3227
    DOI: 10.1039/C7SC05109C

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements