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Borrelidin B: Isolation, Biological Activity, and Implications for Nitrile Biosynthesis

Borrelidin B: Isolation, Biological Activity, and Implications for Nitrile Biosynthesis

Christopher J Schulze, Walter M Bray, Frank Loganzo, My-Hanh Lam, Teresa Szal, Anabella Villalobos, Frank E Koehn, Roger G Linington

J Nat Prod. 2014 Nov 26;77(11):2570-4.

PMID: 25393949

Abstract:

Borrelidin (1) is a nitrile-containing bacterially derived polyketide that is a potent inhibitor of bacterial and eukaryotic threonyl-tRNA synthetases. We now report the discovery of borrelidin B (2), a tetrahydro-borrelidin derivative containing an aminomethyl group in place of the nitrile functionality in borrelidin. The discovery of this new metabolite has implications for both the biosynthesis of the nitrile group and the bioactivity of the borrelidin compound class. Screening in the SToPS assay for tRNA synthetase inhibition revealed that the nitrile moiety is essential for activity, while profiling using our in-house image-based cytological profiling assay demonstrated that 2 retains biological activity by causing a mitotic stall, even in the absence of the nitrile motif.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7184603	Borrelidin		7184-60-3	Price

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