Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling

• Xinli Pan,
• Nicole Domin,
• Sebastian Schieferdecker,
• Hirokazu Kage,
• Martin Roth and
• Markus Nett

Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242

• Biology, Hans Knöll Institute, Beutenbergstr. 11a, 07745 Jena, Germany 10.3762/bjoc.13.242 Abstract The genome of the predatory bacterium Herpetosiphon aurantiacus 114-95T harbors a number of biosynthesis genes, including four terpene cyclase genes. To identify the terpenes biosynthesized from H

• resemblance to cadinane-type sesquiterpenes from plants, but is structurally entirely unprecedented in bacteria. Based on its molecular architecture, a possible biosynthetic pathway is postulated. Keywords: genome mining; herpetopanone; Herpetosiphon; isotope labeling; terpene; Introduction Terpenoids

• predatory bacterium Herpetosiphon aurantiacus 114-95T as a test organism. This strain is capable to produce a variety of polyketides and nonribosomal peptides [13][14][15] and possesses pathways to supply specific building blocks for these natural products [16]. Furthermore, genomic analyses revealed that H

A non-canonical peptide synthetase adenylates 3-methyl-2-oxovaleric acid for auriculamide biosynthesis

• Daniel Braga,
• Dirk Hoffmeister and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 2766–2770, doi:10.3762/bjoc.12.274

• Herpetosiphon aurantiacus. It is composed of three unusual building blocks, including the non-proteinogenic amino acid 3-chloro-L-tyrosine, the α-hydroxy acid L-isoleucic acid, and a methylmalonyl-CoA-derived ethane unit. A candidate genetic locus for auriculamide biosynthesis was identified and encodes four

• enzymatic activity, molecules with methylene α-carbons led to low turnover. Such enzymatic plasticity is an important attribute to help in the perpetual search for novel molecules and to access a greater structural diversity by mutasynthesis. Keywords: adenylation; auriculamide; biosynthesis; Herpetosiphon

• ; nonribosomal peptide synthetase; Findings Herpetosiphon aurantiacus is a filamentous, Gram-negative bacterium with a facultative saprophytic predatory behaviour [1][2]. For a more profound insight into the predation strategies among bacteria, along with the underlying chemistry, the complete genome of H

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• : antibiotics; genome mining; Herpetosiphon; myxobacteria; predation; Introduction Microorganisms are major contributors to primary biomass production and nutrient cycling in nature. The composition of a microbial community shapes an ecosystem, but is also responsive to biotic and environmental cues. Predation

• the history of life, likely preceding eukaryotic predators [6][7][8][9]. Predatory behavior is in fact not uncommon for bacteria. It can be observed in many different species, which are found in the actinobacteria (e.g., Agromyces ramosus) [10], the chloroflexi (e.g., Herpetosiphon spp.) [11][12], the

• [22]. Group predation occurs predominantly in bacteria, which also display social swarming behavior, gliding motility and sophisticated communication systems. Illustrative examples include the myxobacteria, as well as Lysobacter and Herpetosiphon species [6][27][28][29]. Members of these taxa are