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Issue 25, 2014
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An iterative in silico and modular synthetic approach to aqueous soluble tercyclic α-helix mimetics

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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

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Supplementary files

Article information


Submitted
27 Mar 2014
Accepted
11 May 2014
First published
21 May 2014

Org. Biomol. Chem., 2014,12, 4432-4444
Article type
Paper

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

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