Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• source of inspiration for insecticides [1][2]. Among natural product-based insecticides, spinosyns are a novel kind of green insecticides with broad insecticide spectrum. Spinosyns, derivatives of bioactive substances produced by the soil actinomycete Saccharopolyspora spinosa [3], have been widely

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

• in an actinomycete led to a product, which was identified as the soft coral-derived diterpene obscuronatin [25][26]. The biosynthesis of this compound can be easily rationalized via the proposed herpetopanone pathway (route b in Figure 4). Following the formation of the cyclodeca-1,5-diene

Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces

• Enjuro Harunari,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47

• -butyl group. Actinomycete metabolites possessing a contiguous 1,2-diol system. Feeding experiments of 13C-labeled precursors into 1 detected by 2D-INADEQUATE NMR experiments. (a) [1,2-13C2]acetate; (b) [U-13C6]glucose. Organization of the biosynthesis gene cluster for 1. Blue, transcriptional regulator

Evidence for an iterative module in chain elongation on the azalomycin polyketide synthase

• Hui Hong,
• Yuhui Sun,
• Yongjun Zhou,
• Emily Stephens,
• Markiyan Samborskyy and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2016, 12, 2164–2172, doi:10.3762/bjoc.12.206

• from a BAC library of S. malaysiensis DSM4137 genomic DNA as described in Supporting Information File 1, and named pYJ2. To allow the introduction of the cloned azl cluster into actinomycete host strains that are intrinsically resistant to thiostrepton (tsr), the tsr resistance cassette of pYJ2 was

• actinomycete strains. To check for significant deletions in clones housing the azl genes, PCR primer pairs were designed that would anneal approximately every 10 kbp within the gene cluster. The results were fully consistent with the whole gene cluster being present in E. coli ET12567 containing pML1. This

• widely present in actinomycete bacteria. Meanwhile, it is clear that the PKS genes in the azl cluster as sequenced are sufficient to accomplish the synthesis of the full-length azalomycin chain, without requiring any contribution from additional PKS enzymes encoded elsewhere in the S. violaceusniger

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

• : Actinomycete-derived pyridinone natural products are formed in a similar fashion as tetramates (see chapter 2.2.1) [174]. Elaborate polyketide intermediates are condensed to the amine

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• performed a PCR-based screening of a collection of ≈2500 actinomycete strains for similar transaldolase-encoding genes [129]. They could identify the gene sphJ from a Sphaerisporangium sp., which encoded the transaldolase SphJ having 51% amino acid sequence identity with LipK. Following detailed

• characterisation of this enzyme, the sphJ gene was employed as a probe to clone the entire genetic locus consisting of 34 putative ORFs. The expression of three selected genes (including sphJ) was monitored under different growth conditions. Under the thereby identified optimal conditions, the actinomycete

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

• Roseiflexus spp. for the production of natural products is negligible [122], the Herpetosiphon genomes contain a significant number of biosynthetic loci (Table 3). Unlike actinomycete genomes, which are particularly rich in polyketide pathways [123], the Herpetosiphon chromosomes were found to be dominated by

Synthesis of α,β-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction

• Yitao Duan,
• Peiyuan Yao,
• Yuncheng Du,
• Jinhui Feng,
• Qiaqing Wu and
• Dunming Zhu

Beilstein J. Org. Chem. 2015, 11, 2245–2251, doi:10.3762/bjoc.11.243

• report a new CAR from Mycobacterium sp. (Mycobacterium CAR) and its application in a chemo-enzymatic chain elongation method for the preparation of α,β-unsaturated esters by combining an enzymatic carboxylic acid reduction and Wittig reaction. Results and Discussion Nineteen actinomycete strains

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

• Ulrike Groenhagen,
• Michael Maczka,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

• aqueous phase. In our study the volatile bouquet of the actinomycete Streptomyces sp. FORM5 was investigated and several new 2-alkylated pyridines were identified using the closed-loop stripping analysis (CLSA) [7] headspace technique followed by GC–MS analysis and synthesis of the target compounds for

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• subtilis (ATCC 6051 and 6633). Publication of the heronapyrroles was rapidly followed by an account of the biosynthetically related nitropyrrolins A–E, obtained from a different marine-derived actinomycete strain (CNQ-509) (Figure 1) [2]. Of note, the heronapyrroles and nitropyrrolins both feature the same

[²H₂₆]-1-epi-Cubenol, a completely deuterated natural product from Streptomyces griseus

• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2841–2845, doi:10.3762/bjoc.9.319

• Christian A. Citron Jeroen S. Dickschat Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.9.319 Abstract During growth on fully deuterated medium the volatile terpene [2H26]-1-epi-cubenol was released by the actinomycete

• ; terpenes; Introduction The actinomycete Streptomyces griseus is a producer of three terpenes, 2-methylisoborneol (2-MIB, 1), (+)-caryolan-1-ol (2), and (+)-1-epi-cubenol (3, Figure 1). The biosynthesis of 2 and 3 requires the action of well characterized terpene cyclases [1][2], while the biosynthesis of

• deuterated compounds for structure elucidations, biosynthetic or pharmacokinetic investigations that reach far beyond the initially curiosity-driven starting point of this work. Experimental Strain and culture conditions. The actinomycete Streptomyces griseus NBRC102592 was obtained from the National

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

• Tao Wang,
• Patrick Rabe,
• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311

• our work on volatiles from various bacteria and fungi we rarely encountered chlorinated volatiles. Brominated and iodinated volatiles are even more rare. Investigations on the volatiles released by the actinomycete Streptomyces chartreusis during growth on 84 GYM medium, also collected by use of a

• -iodobenzoic acid (1 mM) results in the emission of 23 as the principal volatile compound. Calicheamicin, a known iodinated compound from the actinomycete Micromonspora echinospora. Synthesis of chlorodimethoxybenzenes as reference compounds for X. Synthesis of chlorodimethoxybenzenes as reference compounds

The regulation and biosynthesis of antimycins

• Ryan F. Seipke and
• Matthew I. Hutchings

Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290

• biosynthetic pathway. Keywords: antimycins; gene regulation; genome mining; natural products; Streptomyces; Review It is estimated that around 60% of all known antibiotics are derived from secondary metabolites made by filamentous actinomycete bacteria, most notably Streptomyces species [1]. Streptomyces

• antAB and antCDE is a transcriptional activator that is encoded outside of the ant gene cluster and is absent from the heterologous host strains (Seipke and Hutchings, unpublished results). Regulation of antibiotic gene clusters by ECF σ factors has only been reported in two rare actinomycete strains

Quantification of N-acetylcysteamine activated methylmalonate incorporation into polyketide biosynthesis

• Stephan Klopries,
• Uschi Sundermann and
• Frank Schulz

Beilstein J. Org. Chem. 2013, 9, 664–674, doi:10.3762/bjoc.9.75

• concentrations of (S)-4 between the two fermentations (typically ≥1 mM). This indicates a sufficient reactivity with PKS. However, when considering that the compound competes with endogenous MM-CoA, which is present at micromolar concentration in actinomycete cells [43], it is apparent that analogous malonate

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• methylmalonyl-CoA was determined by feeding experiments [14]. During our ongoing analysis of the volatiles released by different bacteria and fungi with high potential for secondary metabolism, the actinomycete Micromonospora aurantiaca ATCC 27029 came to our attention. This gram-positive, sporulating bacterial

• actinomycete M. aurantiaca ATCC 27029 were collected by use of a closed-loop stripping apparatus (CLSA), as described previously [17][18], and the obtained headspace extracts were analysed by GC–MS. The structures of the identified compounds (apart from FAMEs, which will be discussed below) are shown in Figure

Phaeochromycins F–H, three new polyketide metabolites from Streptomyces sp. DSS-18

• Jian Li,
• Chun-Hua Lu,
• Bao-Bing Zhao,
• Zhong-Hui Zheng and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2008, 4, No. 46, doi:10.3762/bjoc.4.46

• ), H (3), were obtained from the culture broth of marine actinomycete strain Streptomyces sp. DSS-18. Their structures were established on the basis of detailed spectroscopic analyses, including 1D-, 2D-NMR and HR-ESI MS techniques. Keywords: biological properties; isolation; polyketides; Streptomyces