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Issue 21, 2012
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Elucidation of post-PKS tailoring steps involved in landomycin biosynthesis

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Abstract

The functional roles of all proposed enzymes involved in the post-PKS redox reactions of the biosynthesis of various landomycin aglycones were thoroughly studied, both in vivo and in vitro. The results revealed that LanM2 acts as a dehydratase and is responsible for concomitant release of the last PKS-tethered intermediate to yield prejadomycin (10). Prejadomycin (10) was confirmed to be a general pathway intermediate of the biosynthesis. Oxygenase LanE and the reductase LanV are sufficient to convert 10 into 11-deoxylandomycinone (5) in the presence of NADH. LanZ4 is a reductase providing reduced flavin (FMNH) co-factor to the partner enzyme LanZ5, which controls all remaining steps. LanZ5, a bifunctional oxygenase–dehydratase, is a key enzyme directing landomycin biosynthesis. It catalyzes hydroxylation at the 11-position preferentially only after the first glycosylation step, and requires the presence of LanZ4. In the absence of such a glycosylation, LanZ5 catalyzes C5,6-dehydration, leading to the production of anhydrolandomycinone (8) or tetrangulol (9). The overall results provided a revised pathway for the biosynthesis of the four aglycones that are found in various congeners of the landomycin group.

Graphical abstract: Elucidation of post-PKS tailoring steps involved in landomycin biosynthesis

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Publication details

The article was received on 23 Dec 2011, accepted on 02 Mar 2012 and first published on 05 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB07171A
Citation: Org. Biomol. Chem., 2012,10, 4256-4265
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    Elucidation of post-PKS tailoring steps involved in landomycin biosynthesis

    M. K. Kharel, P. Pahari, K. A. Shaaban, G. Wang, C. Morris and J. Rohr, Org. Biomol. Chem., 2012, 10, 4256
    DOI: 10.1039/C2OB07171A

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