Natural metabolic diversity encoded by the enterocin biosynthesis gene cluster [15]

Journal of the American Chemical Society

Volumn 122, Issue 22, 2000, Pages 5415-5416

  Piel, Jörn ^a,b   Hoang, Khanh ^b   Moore, Bradley S ^b,c  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^b UNIVERSITY OF WASHINGTON   (United States)

^c UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; BENZOIC ACID DERIVATIVE; POLYKETIDE;

BIOSYNTHESIS; GENE CLUSTER; LETTER; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; RESTRICTION FRAGMENT; STEREOCHEMISTRY;

EID: 0034616778     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000445n     Document Type: Letter

References (21)

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2. The bacterium has recently been described as a new species within the genus Streptomyces on the basis of cultural characteristics, physiological characteristics, and 16S rDNA analysis (AF233338).
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9. S. lividans K4-114 was generously provided by Dr. M. C. Betlach, Kosan Biosciences, Inc., Hay ward, CA. This host lacks the entire actinorhodin biosynthesis gene cluster and displays a negligible level of background polyketide synthesis. (Ziermann, R.; Betlach, M. C. BioTechniques 1999, 26, 106).
10. 5-benzoate-containing Al plate. The crude EtOAc extracts were subjected to silica gel flash chromatography and eluted with EtOAc and MeOH. The fractions containing enterocin-like compounds were combined, dried, dissolved in MeOH (0.5 mL), and analyzed (3 μL). A Hewlett-Packard HP1100 LC pump with a diode-array detector was linked to a Bruker HP Esquire LC mass spectrometer operating in the negative ion mode. A Beckman Ultrasphere C18 column (4.6 mm × 15 cm) was used at a flow rate of 1 mL/min with a linear solvent gradient of 5% MeOH in 0.15% trifluoroacetic acid-water to 100% MeOH over a period of 45 min.
11. "S. maritimus" was grown in 500 mL Erlenmeyer flasks containing 100 mL of Al media on a rotary shaker at 200 rpm for 3 d at 26 °C. The liquid culture (2 L) was extracted with EtOAc (3 × 500 mL), and the resulting crude extract was subjected to silica flash chromatography using hexane/ EtOAc/MeOH mixtures. Further purification of mixed fractions was achieved by reversed-phase HPLC (Alltech Ultrasphere C18, 5 μ 4.6 mm × 25 cm) with a 63-100% MeOH in 0.1% acetic acid solvent gradient run at 4.5 mL/ min to yield wailupemycin D (5 mg).
12. 6) δ 51.5 (C14), 55.4 (C6), 76.2 (C15), 89.9 (C2), 105.3 (C4), 117.2 (C12), 117.3 (C10), 120.4 (C8), 126.3 (C17/17′), 128.2 (C19), 128.9 (C18/18′), 137.4(C9), 143.3 (C7), 145.9 (C16), 162.3 (C11), 164.1 (C5), 164.7 (C1), 171.6 (C3), 204.5 (C13).
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18. The GenBank accession number for the enc cluster is AF254925.
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