Structure and absolute configuration of auriculamide, a natural product from the predatory bacterium Herpetosiphon aurantiacus.

Schieferdecker S, Domin N, Hoffmeier C, Bryant DA, Roth M, Nett M (2015) Structure and absolute configuration of auriculamide, a natural product from the predatory bacterium Herpetosiphon aurantiacus. Eur J Org Chem 14, 3057-3062.

Abstract

The genome of the filamentous, predatory bacterium Herpetosiphon aurantiacus harbors a plethora of genes that are predicted to be involved in natural product biosynthesis. Until now, however, no secondary metabolites have been described from this microorganism. Analysis of H. aurantiacus culture extracts by 1H NMR spectroscopy now led to the discovery of a chlorinated amide, which we termed auriculamide. The configuration of the three chiral centers in auriculamide was solved by chromatographic comparison with stereospecifically prepared reference compounds following chemical degradation. Furthermore, a putative gene cluster for the biosynthesis of auriculamide was identified by genome mining.

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doi: 10.1002/ejoc.201500181