New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita

• Frank Surup,
• Florian Hennicke,
• Nadine Sella,
• Maria Stroot,
• Steffen Bernecker,
• Sebastian Pfütze,
• Marc Stadler and
• Martin Rühl

Beilstein J. Org. Chem. 2019, 15, 1000–1007, doi:10.3762/bjoc.15.98

• clusters. Keywords: bioinformatics; gene cluster analysis; natural products; secondary metabolites; structure elucidation; terpenes; Introduction The basidiomycete Agrocybe aegerita (synonym: A. cylindracea) was traditionally accommodated in the genus Agrocybe (family Bolbitiaceae) until a recent

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• formation of up to two new stereocentres. Its appearance in several polyketide biosynthetic pathways was proposed for a decade based on gene cluster analysis. An in vitro characterisation of responsible catalytic units has however only recently been achieved. Two pyran-forming cyclase domains were

• salinosporamide A (199) (Scheme 27) [160][161]. Based on gene cluster analysis, it was proposed that both heterocycles of this PKS–NRPS hybrid product, an oxetan-2-one and a pyrrolidin-2-one, are formed by a bicyclisation mechanism. Aldol addition of the amino acid α-position on the carbonyl gives the pyrrolidin

• available from the gene cluster analysis of the O-methylated, highly substituted α-pyridinone piericidin A1 (221) from Streptomyces piomogeues var. Hangzhouwanensis (Scheme 30b) [165][166]. Apart from the genes that code for a modular type I PKS as well as O-methyltransferases and an oxygenase, the cluster

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• cluster analysis also revealed that pederin is formed by an enzyme belonging to a functionally and evolutionarily novel group termed trans-acyltransferase PKSs (trans-AT PKSs) [24][52]. The structurally related compound diaphorin (4) was later found in a study of the defensive symbiosis between the Asian

• molecular analysis of the biosynthetic gene cluster of pederin (3) [49][50][51][52]. Beetle larvae hatching from pederin-containing eggs were less prone to predation by wolf spiders than pederin-free larvae, indicating the ecological significance of this secondary metabolite [53]. The biosynthetic gene

Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis

• Frank Hahn,
• Nadine Kandziora,
• Steffen Friedrich and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 634–640, doi:10.3762/bjoc.10.55

• biosynthesis, we became interested in the formation of the (12Z,14E)-diene [7]. Z-configured double bonds are much rarer in polyketides than their E-configured counterparts, and their biosynthesis has not been thoroughly investigated yet [7][8][9]. Gene cluster analysis suggested that the double bond at