The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• . Venustatriol (96) could then be obtained by C–C-coupling with the corresponding THP fragment in an enantioselective fashion. Glaciapyrrol A Glaciapyrrol A (100), B and C form a family of pyrrolo sesquiterpenoids which have been isolated in 2005 from a marine Streptomyces sp. (NPS008187) by Macherla et al. [161

Mechanistic investigations on six bacterial terpene cyclases

• Patrick Rabe,
• Thomas Schmitz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173

• relative of the enzyme from S. viridochromogenes is found in Streptomyces sp. NRRL S-481 (86% identity). Incubation of FPP with a recombinant terpene synthase from Roseiflexus castenholzii DSM 13941 (accession number WP_012119179) resulted in the formation of the sesquiterpene alcohol 2, previously

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

• Atul A. Dhavan,
• Rahul D. Kaduskar,
• Loana Musso,
• Leonardo Scaglioni,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2016, 12, 1624–1628, doi:10.3762/bjoc.12.159

• ]. Chemical analysis of a terrestrial-derived Streptomyces sp. isolated from the rhizosphere of the plant Juniperus excelsa yielded a new metabolite, leopolic acid A (1, Figure 1) [2]. Leopolic acid has unprecedented structural features consisting of an aliphatic side chain attached to a 2,3-pyrrolidinedione

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

• discussed. Review Structures of naturally occurring muraymycins The muraymycins were first isolated in 2002 from a broth of a Streptomyces sp. [22]. McDonald et al. discovered and characterised 19 naturally occurring muraymycins (Figure 1). These compounds belong to the family of nucleoside antibiotics

• ]. Biosynthesis So far, there are only limited insights into muraymycin biosynthesis. The biosynthetic gene cluster for the formation of muraymycins in Streptomyces sp. NRRL 30471 has been identified by Chen, Deng et al. in 2011 [118]. The sequence analysis revealed the cluster to contain 33 open reading frames

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• -pyran-2-one (47, Figure 10) [52]. Also antitumor activities of α-pyrones had been shown. Thus, pironetin (47, Figure 10) induced apoptosis in a dose- and time-dependent manner, and tubulin assembly was inhibited in vitro [53]. The natural product was isolated from Streptomyces sp. NK10958 [54], and its

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

• Ulrike Groenhagen Michael Maczka Jeroen S. Dickschat Stefan Schulz Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.10.146 Abstract Streptomyces sp. FORM5 is a bacterium that is known to produce the antibiotic streptazolin

• [2] such as methyl pyrrole-2-carboxylate, emitted by Stackebrandtia nassauensis, or 2-acetylpyrrole from Saccharopolyspora erythraea, volatile alkaloids are rarely produced by actinomycetes. We became interested in the strain Streptomyces sp. FORM5 to elucidate whether volatile formation is linked to

• 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

• /bjoc.10.121 Abstract The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the

• : biomimetic synthesis; biosynthesis; heronapyrroles; microbial biodiscovery; natural products; nitropyrroloterpenes; Introduction Heronapyrroles A–C (Figure 1) were first reported in 2010 by Capon et al. from a marine-derived Streptomyces sp. (CMB-M0423) obtained from a shallow water sand sample collected

• initiate a cyclization cascade [1][3][8] that would provide the bis-tetrahydrofuran heronapyrrole C (Scheme 1), via a mechanism that closely resembles polyether antibiotic biosynthesis [12][13][14][15][16][17]. This biosynthetic hypothesis raises the possibility that Streptomyces sp. (CMB-M0423) may

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• isomers – cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) – and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However

• ; geometrical isomer; natural products; Streptomyces sp. LZ35; Introduction Cuevaenes are polyketides containing 3-hydroxybenzoic acid (3-HBA). Only 4 naturally occurring cuevaenes are described. Cuevaenes A and B were isolated from Streptomyces sp. HKI 0180 fifteen years ago and display moderate antibacterial

• activity against Gram-positive bacteria [1]. JBIR-23 and JBIR-24, novel anti-malignant pleural mesothelioma (MPM) agents, were isolated from Streptomyces sp. AK-AB27 six years ago [2]. All of these natural products have a tricyclic core and a polyene side chain with an enolmethyl ether inside. This type of

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

• . gancidicus BKS 13–15 and S. griseoflavus Tü4000 [23]. Interestingly, S. hygroscopicus subsp. jinggangensis 5008 and S. hygroscopicus subsp. jinggangensis TL01 encode L-form ant gene clusters, but do not encode AntE (Figure 2). I-form ant gene clusters are encoded by two species, Streptomyces sp. 303MFCol5.2

• and Streptomyces sp. TOR3209, which lack antQ and antP, respectively (Figure 2). There are six taxa, all highly related to S. albus S4, that encode S-form ant gene clusters: S. albus S4 [7], S. albus J1074 [7], Streptomyces sp. SM8, Streptomyces sp. NRRL2288 [25], Streptomyces sp. LaPpAH-202 and

• Streptomyces sp. CNY228. Based on our analysis of S. albus S4, the S-form gene cluster is organised into four transcriptional units; antAB, antCDE, antFG and antHIJKLMNO (Seipke and Hutchings, unpublished results; Figure 2). The antFGHIJKLN genes encode the biosynthesis pathway for the unusual starter unit, 3

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• napyradiomycin biosynthesis gene cluster from S. aculeolatus [30], and fur18 in the biosynthetic gene cluster of furaquinocin A from Streptomyces sp. KO-3988 [31]. A similar gene, aur1O, is found in the biosynthetic gene cluster of the polyketide antibiotic auricin from S. aureofaciens [32]. The function of

Tertiary alcohol preferred: Hydroxylation of trans-3-methyl-L-proline with proline hydroxylases

• Christian Klein and
• Wolfgang Hüttel

Beilstein J. Org. Chem. 2011, 7, 1643–1647, doi:10.3762/bjoc.7.193

• ][23][24]. So far, five bacterial proline hydroxylases have been cloned and overexpressed in E. coli: A trans-4-proline hydroxylase (trans-P4H) from Dactylosporangium sp. [25] two cis-3-proline hydroxylase isoenzymes from Streptomyces sp. strain TH1 (cis-P3H_I and cis-P3H_II) [26][27] and two cis-4

Stereoselective synthesis of four possible isomers of streptopyrrolidine

• Debendra K. Mohapatra,
• Barla Thirupathi,
• Pragna P. Das and
• Jhillu S. Yadav

Beilstein J. Org. Chem. 2011, 7, 34–39, doi:10.3762/bjoc.7.6

• Streptomyces sp. found in deep sea sediments [12]. The system is present in many biologically active compounds [13][14][15][16][17][18][19][20][21] and it could act as a versatile intermediate for the synthesis of a wide range of γ-amino acids as well as pyrrolidines [22][23]. The interesting chemical

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

• Streptomyces sp. DSS-18 (see Figure 1). Results and Discussion Fermentation was carried out at 28 °C for 2 weeks with aeration (10 L/min) under constant agitation (240 rpm). After filtration of the harvested culture broth, the culture filtrate was extracted exhaustively with ethyl acetate. The ethyl acetate

• : Bruker HR-ESI mass spectrometer; in m/z. Fermentation and Isolation of the Strain The strain Streptomyces sp. DSS-18 was isolated from the sediment collected from West Pacific Ocean and was identified as Streptomyces sp. according to its 16S rDNA sequence (bankit1156038 FJ472840). Genomic DNA of strains