Jump to main content
Jump to site search

Issue 25, 2014
Previous Article Next Article

An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics

Author affiliations

Abstract

Tercyclic scaffolds, designed to have improved synthetic accessibility and aqueous solubility, were evaluated as structural α-helix mimetics by using an iterative in silico approach. The synthesis of these tercyclic scaffolds was accomplished using a modular synthetic approach by employing functionalised methoxyphenyl units which were readily manipulated to allow the introduction of various nitrogen-based heterocycles. The ability of these scaffolds to mimic the key i, i + 3 and i + 7 residues of a polyalanine α-helix was ratified by in silico studies, X-ray crystallographic and NOESY analysis, and their aqueous solubility was measured by a kinetic turbidimetric method.

Graphical abstract: An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Mar 2014, accepted on 11 May 2014 and first published on 21 May 2014


Article type: Paper
DOI: 10.1039/C4OB00647J
Citation: Org. Biomol. Chem., 2014,12, 4432-4444
  •   Request permissions

    An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics

    Z. Lim, P. J. Duggan, A. G. Meyer and K. L. Tuck, Org. Biomol. Chem., 2014, 12, 4432
    DOI: 10.1039/C4OB00647J

Search articles by author

Spotlight

Advertisements