Enhancing structural diversity of terpenoids by multisubstrate terpene synthases

• Min Li and
• Hui Tao

Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86

• ), hammershoyl diphosphate (111), and ancheryl diphosphate (112) (Figure 8c). Subsequently, terpentetriene synthase from Kitasatospora griseola (Cyc2) and kolavelool synthase from Herpetosiphon aurantiacus (HaKS) were identified as capable of converting these building blocks into C16 scaffolds, whereas other

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