Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 25, 2014

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

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements