Jump to main content
Jump to site search

Issue 5, 2016
Previous Article Next Article

Peptidines: glycine-amidine-based oligomers for solution- and solid-phase synthesis

Author affiliations

Abstract

Efforts to emulate biological oligomers have given rise to a host of useful technologies, ranging from solid-phase peptide and nucleic acid synthesis to various peptidomimetic platforms. Herein we introduce a novel class of peptide-like oligomers called “peptidines” wherein each carbonyl O-atom within poly-N-alkyl glycine oligomers is replaced with a functionalized N-atom. Compared to peptoids or peptides, the presence of this amidine N-substituent in peptidines effectively doubles the number of diversification sites per monomeric unit, and can decrease their overall conformational flexibility. We have developed iterative solution- and solid-phase protocols for the straightforward assembly of peptidines containing diverse backbone and amidine substituents, derived from readily available primary and secondary amines. We have also performed crystallographic and computational studies, which demonstrate a strong preference for the trans (E) amidine geometry. Given their straightforward synthetic preparation and high functional group density, peptidines have the potential to serve as useful tools for library generation, peptide mimicry, and the identification of biologically active small molecules.

Graphical abstract: Peptidines: glycine-amidine-based oligomers for solution- and solid-phase synthesis

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Oct 2015, accepted on 31 Jan 2016 and first published on 16 Feb 2016


Article type: Edge Article
DOI: 10.1039/C5SC03882K
Citation: Chem. Sci., 2016,7, 3317-3324
  • Open access: Creative Commons BY license
  •   Request permissions

    Peptidines: glycine-amidine-based oligomers for solution- and solid-phase synthesis

    J. Vastl, R. Kartika, K. Park, A. E. Cho and D. A. Spiegel, Chem. Sci., 2016, 7, 3317
    DOI: 10.1039/C5SC03882K

    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