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Issue 4, 2009
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Solid-phase synthesis of a library of linear oligoester ion-channels

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Abstract

A solid-phase synthesis protocol was used to prepare fifteen new linear tetra-, and penta-esters structurally related to an active lead compound. The structures were assembled from three types of hydroxyl protected building blocks: monoalkyl esters of hydroxyglutaric acid, ω-hydroxyacids, and α-hydroxymethylalkanoic acids. The standard methodology gave acceptable quantities of material free of small molecule impurities. Mass spectrometric analysis revealed the presence of deletions due to incomplete coupling, as well as additions and macrolactones due to partial acidic rearrangement on release from the solid-support. The amount of these impurities could be estimated from the 1H NMR spectra, and their implications for subsequent activity analysis are discussed.

Graphical abstract: Solid-phase synthesis of a library of linear oligoester ion-channels

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Publication details

The article was received on 23 Sep 2008, accepted on 10 Nov 2008 and first published on 19 Jan 2009


Article type: Paper
DOI: 10.1039/B816648J
Citation: Org. Biomol. Chem., 2009,7, 725-732
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    Solid-phase synthesis of a library of linear oligoester ion-channels

    T. M. Fyles and H. Luong, Org. Biomol. Chem., 2009, 7, 725
    DOI: 10.1039/B816648J

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