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Issue 18, 2008
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Engineered biosynthesis of hybrid macrolide polyketides containing D-angolosamine and D-mycaminose moieties

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Abstract

The glycosylation of natural product scaffolds with highly modified deoxysugars is often essential for their biological activity, being responsible for specific contacts to molecular targets and significantly affecting their pharmacokinetic properties. In order to provide tools for the targeted alteration of natural product glycosylation patterns, significant strides have been made to understand the biosynthesis of activated deoxysugars and their transfer. We report here efforts towards the production of plasmid-borne biosynthetic gene cassettes capable of producing TDP-activated forms of D-mycaminose, D-angolosamine and D-desosamine. We additionally describe the transfer of these deoxysugars to macrolide aglycones using the glycosyl transferases EryCIII, TylMII and AngMII, which display usefully broad substrate tolerance.

Graphical abstract: Engineered biosynthesis of hybrid macrolide polyketides containing d-angolosamine and d-mycaminose moieties

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Publication details

The article was received on 09 May 2008, accepted on 24 Jun 2008 and first published on 28 Jul 2008


Article type: Paper
DOI: 10.1039/B807914E
Citation: Org. Biomol. Chem., 2008,6, 3315-3327
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    Engineered biosynthesis of hybrid macrolide polyketides containing D-angolosamine and D-mycaminose moieties

    U. Schell, S. F. Haydock, A. L. Kaja, I. Carletti, R. E. Lill, E. Read, L. S. Sheehan, L. Low, M. Fernandez, F. Grolle, H. A. I. McArthur, R. M. Sheridan, P. F. Leadlay, B. Wilkinson and S. Gaisser, Org. Biomol. Chem., 2008, 6, 3315
    DOI: 10.1039/B807914E

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