An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine

• Jörg Erdsack and
• Norbert Krause

Beilstein J. Org. Chem. 2013, 9, 1936–1942, doi:10.3762/bjoc.9.229

• ; amino acids; cuprates; furanomycin; gold catalysis; Introduction In 1967, Katagiri et al. reported the isolation of a novel antibiotic from the culture broth of the fungus Streptomyces threomyceticus [1]. The compound acts as a competitive antagonist for isoleucine in vitro and hampers the growth of

Activation of cryptic metabolite production through gene disruption: Dimethyl furan-2,4-dicarboxylate produced by Streptomyces sahachiroi

• Dinesh Simkhada,
• Huitu Zhang,
• Shogo Mori,
• Howard Williams and
• Coran M. H. Watanabe

Beilstein J. Org. Chem. 2013, 9, 1768–1773, doi:10.3762/bjoc.9.205

• ; Streptomyces; Findings It has become increasingly apparent that microbial diversity in nature far exceeds that reflected in laboratory strain collections. The advent of microbial genomics and the availability of published genome sequences suggest, that as much as 90% of the chemical potential of these

• precursors of the orphan pathway are fed to the organism and used to screen extracts of the fermentation broth, to identify metabolites containing the labeled precursors [9][10]. Here, we have carried out a functional knockout of aziA2 within the azinomycin gene cluster of Streptomyces sahachiroi [11][12

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

• of the fermentation extracts, the incorporation was to be quantified in an erythromycin-producing strain of Saccharopolyspora erythraea (NRRL B-24071) and a rapamycin-producing strain of Streptomyces hygroscopicus (NRRL 5491) through the corresponding shift in the isotope ratio. For feeding

• ) and the supernatant was dried in vacuo. The residue was redissolved in 1 mL methanol, filtered and used for analysis. Rapamycin: Streptomyces hygroscopicus NRRL 5491 was grown on SY agar [46] at 28 °C. Fermentation was carried out in 50 mL Erlenmeyer flasks containing a steel spring. A 0.5 cm × 0.5 cm

Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes

• Tony Taldone,
• Anna Rodina,
• Erica M. DaGama Gomes,
• Matthew Riolo,
• Hardik J. Patel,
• Raul Alonso-Sabadell,
• Danuta Zatorska,
• Maulik R. Patel,
• Sarah Kishinevsky and
• Gabriela Chiosis

Beilstein J. Org. Chem. 2013, 9, 544–556, doi:10.3762/bjoc.9.60

• . Results and Discussion Design and synthesis of biotinylated purine scaffold Hsp90 probes Geldanamycin (GM) is a benzoquinone ansamycin first isolated from a fermentation broth of Streptomyces hygroscopicus [15] and was the first reported Hsp90 inhibitor [16]. It has played a paramount role as a probe

Caryolene-forming carbocation rearrangements

• Quynh Nhu N. Nguyen and
• Dean J. Tantillo

Beilstein J. Org. Chem. 2013, 9, 323–331, doi:10.3762/bjoc.9.37

• , Streptomyces bacteria, Sinacalia tangutica plants, and Eurypon sponges (Figure 1) [3][4][5][6]. The carbon skeleton of 1 is unusual, not only because it contains concatenated 4-, 6-, and 7-membered rings, but also in that it bears a bridgehead double bond. As noted in the original isolation report [2], this

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• was isolated from Streptomyces roseochromogenes R-468 and S. lavendulae SF-425 in the 1960s [5], this class of compounds has attracted a great deal of interest in the medical community due to their promising pharmaceutical potential as antidiabetic [6], antitumor [7] and antiviral [8] agents

Synthetic studies towards bottromycin

• Stefanie Ackermann,
• Hans-Georg Lerchen,
• Dieter Häbich,
• Angelika Ullrich and
• Uli Kazmaier

Beilstein J. Org. Chem. 2012, 8, 1652–1656, doi:10.3762/bjoc.8.189

• fermentation broth of Streptomyces bottropensis, called bottromycin [4][5][6]. This antibiotic inhibits the growth of a wide range of microorganisms by interfering with their protein biosynthesis [7][8][9][10][11][12]. In 1965 Nakamura et al. isolated closely related antibiotics from the strain Streptomyces No

Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations

• Tobias Knobloch,
• Gerald Dräger,
• Wera Collisi,
• Florenz Sasse and
• Andreas Kirschning

Beilstein J. Org. Chem. 2012, 8, 861–869, doi:10.3762/bjoc.8.96

• ansamitocin producer [13][14][15][16][17], and Streptomyces hygroscopicus, the geldanamycin producer [18][19]. These engineered strains are unable to biosynthesize 3-amino-5-hydroxybenzoic acid (1) [20], the common starter unit for both polyketide synthases (PKS) (Scheme 1). These assembly-line-type

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

• Zhiyuan Ma,
• Feng Ni,
• Grace H. C. Woo,
• Sie-Mun Lo,
• Philip M. Roveto,
• Scott E. Schaus and
• John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

• grossularia (Stylidae) [1][2], and desmethylgrossularine-1 from tunicate Polycarpa aurata [3]. Other natural α-carbolines include mescengricin (3), an inhibitor of L-glutamate excitotoxicity in neutrons, isolated from Streptomyces griseoflavus [4], and cryptotackieine (4) [5], also known as neocryptolepine [6

Identification and isolation of insecticidal oxazoles from Pseudomonas spp.

• Florian Grundmann,
• Veronika Dill,
• Andrea Dowling,
• Aunchalee Thanwisai,
• Edna Bode,
• Narisara Chantratita,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 749–752, doi:10.3762/bjoc.8.85

• identified in this article, are not only prevalent in Pseudomonas but also in other bacteria such as Streptomyces [20] or Streptoverticillium [8][10], suggesting a biological relevance also in these bacteria. However, as concluded from the observed activity against insect cells, they could significantly add

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

• , 72076 Tübingen, Germany 10.3762/bjoc.8.57 Abstract The biosynthetic gene cluster for endophenazines, i.e., prenylated phenazines from Streptomyces anulatus 9663, was heterologously expressed in several engineered host strains derived from Streptomyces coelicolor M145. The highest production levels were

• the first investigation of the regulatory genes of phenazine biosynthesis in Streptomyces. Keywords: phenazine; gene cluster; gene inactivation; Introduction Phenazine natural products have important biological activities comprising antibacterial, antifungal, antitumor, antimalarial, antioxidant and

• phenazines are secondary metabolites, produced mainly by different species of the proteobacterium Pseudomonas and of the actinobacterium Streptomyces. While Pseudomonas strains produce phenazine derivatives with relatively simple structures, more complex phenazines are produced by Streptomyces strains [1

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

Metathesis access to monocyclic iminocyclitol-based therapeutic agents

• Ileana Dragutan,
• Valerian Dragutan,
• Carmen Mitan,
• Hermanus C.M. Vosloo,
• Lionel Delaude and
• Albert Demonceau

Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81

• , nojirimycin (NJ, trivial name for 5-amino-5-deoxy-D-glucopyranose) (59), the first alkaloid discovered that mimicks a sugar (originally isolated from Streptomyces filtrate but also found in other bacterial cultures and plant sources), is a potent glycosidase inhibitor. In aqueous solution nojirimycin exists

Application of the diastereoselective photodeconjugation of α,β-unsaturated esters to the synthesis of gymnastatin H

• Ludovic Raffier and
• Olivier Piva

Beilstein J. Org. Chem. 2011, 7, 151–155, doi:10.3762/bjoc.7.21

• manumycin C (12) isolated from Streptomyces parvulus [13]. Different groups have investigated the synthesis of gymnastatins 10a–c [14][15][16], compounds 11 [17] and 12 [18]. In most cases, the lateral acid chain was prepared starting from (R)-2-methyloctanal by iterative Wittig reactions to build the

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

One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

• Priyabrata Roy and
• Binay Krishna Ghorai

Beilstein J. Org. Chem. 2010, 6, No. 52, doi:10.3762/bjoc.6.52

• heterocycles which exhibit a wide range of biological activities. Many phenazine compounds are found in nature and are produced by bacteria such as Pseudomonas spp., Streptomyces spp. and Pantoea agglomerans. These phenazine natural products have been implicated in the virulence and competitive fitness of the

Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

• Pitak Nasomjai,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2009, 5, No. 37, doi:10.3762/bjoc.5.37

• bacterium Streptomyces cattleya as part of its defense strategy since 4-fluorothreonine (2) has antibiotic activity and fluoroacetate (1) is a toxin [1]. The biosynthetic pathway from fluoride ion to these fluorometabolites has largely been elucidated and is summarised in Scheme 1 [2]. The first committed

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• . Discussion 1. Mitomycin isolation and nomenclature Mitomycins are natural products isolated from extracts of genus Streptomyces, a filamentous gram-positive soil bacterium that produces a wide array of biologically active compounds, including over two-thirds of the commercially important natural-product

• metabolites [21]. Mitomycin C is extracted from the bacterium Streptomyces lavendulae and is far from the most known compound of the series. It has become one of the most effective drugs against non-small-cell lung carcinoma, as well as other soft and solid tumours [22]. The seven most abundant mitomycins (A

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

• from marine derived actinomycetes, a strain of the genus Streptomyces was isolated from deep sediment collected from the west Pacific. Herein, we report the isolation and structure determination and biological properties of three new polyketides, namely phaeochromycins F (1), G (2) and H (3), from

• 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

Diels- Alder reactions using 4,7-dioxygenated indanones as dienophiles for regioselective construction of oxygenated 2,3-dihydrobenz[f]indenone skeleton

• Natsuno Etomi,
• Takuya Kumamoto,
• Waka Nakanishi and
• Tsutomu Ishikawa

Beilstein J. Org. Chem. 2008, 4, No. 15, doi:10.3762/bjoc.4.15

• acid-induced ring opening to give 2,3-dihydrobenz[f]indenone with undesired 4,5,9-trioxy functions. Background Kinamycins, isolated from Streptomyces murayamaensis sp. nov. Hata et Ohtani in 1970 [1][2][3], have attracted attention due to their antibiotic and antitumor activities [7][8][9][10]. These