Nanaomycin D
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| Category | Antibiotics |
| Catalog number | BBF-01983 |
| CAS | 60325-08-8 |
| Molecular Weight | 300.26 |
| Molecular Formula | C16H12O6 |
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Description
Nanaomycin D is an antibiotic produced by Str. rosa subsp. notoensis. It has antibacterial activity.
Specification
| IUPAC Name | (11R,15S,17S)-4-hydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione |
| Canonical SMILES | CC1C2=C(C3C(O1)CC(=O)O3)C(=O)C4=C(C2=O)C(=CC=C4)O |
| InChI | InChI=1S/C16H12O6/c1-6-11-13(16-9(21-6)5-10(18)22-16)14(19)7-3-2-4-8(17)12(7)15(11)20/h2-4,6,9,16-17H,5H2,1H3/t6-,9-,16-/m0/s1 |
| InChI Key | XUWPJKDMEZSVTP-UOSCCXBLSA-N |
Properties
| Antibiotic Activity Spectrum | bacteria |
| Boiling Point | 624.5±55.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Cloning of large DNA fragments, which hybridize with actinorhodin biosynthesis genes, from kalafungin and nanaomycin A methyl ester producers and identification of genes for kalafungin biosynthesis of the kalafungin producer
S Kakinuma, Y Takada, H Ikeda, H Tanaka, S Omura, D A Hopwood J Antibiot (Tokyo). 1991 Sep;44(9):995-1005. doi: 10.7164/antibiotics.44.995.
Large actI, III-homologous DNA fragments were isolated from genomic libraries of the strains that produce the benzoisochromanequinone antibiotics kalafungin and nanaomycin A methyl ester, Streptomyces tanashiensis strain Kala and Streptomyces sp. OM-173, respectively. These libraries were prepared in Escherichia coli JM108 by using a novel Streptomyces-E. coli bifunctional cosmid, pKU205, and screened with polyketide synthase genes (actI and III) for actinorhodin biosynthesis from Streptomyces coelicolor A3(2) as probes. The cloned DNA fragments (28 and 42 kb) were analyzed by hybridization with DNA containing actinorhodin biosynthetic genes (actI, II, III, IV, VA, VB, VI and VII). Both fragments hybridized with the actI, III, VA and VI regions, but not with the actII, IV, VB and VII regions. The cloned fragment of S. tanashiensis DNA was analyzed by complementation tests with kalafungin-nonproducing mutants. Seven genes (kalI approximately VII), which correspond to seven steps in kalafungin biosynthesis, were found to be located on a 14 kb continuous DNA fragment. Five of the genes were located on the regions homologous to the genes for actinorhodin biosynthesis, but the other two genes were not. Although kalafungin is an intermediate or shunt product in actinorhodin biosynthesis in S. coelicolor A3(2), the genes for kalafungin biosynthesis in S. tanashiensis are not identical with those in S. coelicolor A3(2).
2. Isolation of restriction-reduced mutants from Streptomyces
S Kakinuma, H Ikeda, H Tanaka, S Omura Agric Biol Chem. 1990 Oct;54(10):2611-7.
Restriction-reduced mutants were isolated from Streptomyces rosa subsp. notoensis KA301 and S. tanashiensis strain Kala which produce the benzoisochromanequinone antibiotics nanaomycin and kalafungin, respectively. The mutants of S. rosa, which can be transformed with a multi-copy plasmid and in which the actinophage Pa16 can propagate, were selected. They were transformed with a single-copy plasmid propagated in S. lividans TK24, and with its modified plasmid propagated in the mutant at higher efficiency. The mutants of S. tanashiensis were selected by their capability to be transformed with a multi-copy plasmid. The efficiency of transformation with a single-copy plasmid propagated in S. lividans TK24 was low, but was much increased by heating the protoplasts at 42 degrees C for 15 min prior to the transformation. These mutants derived from both strains probably lack at least one of their restriction systems.
3. Halawanones A-D, new polycyclic quinones from a marine-derived streptomycete
PW Ford, M Gadepalli, BS Davidson J Nat Prod. 1998 Oct;61(10):1232-6. doi: 10.1021/np980126y.
Four new quinone-containing metabolites, halawanones A-D (1-4), have been isolated along with the known compound nanaomycin D (5) from liquid cultures of a streptomycete obtained from a sediment sample collected in the estuarine environment at the mouth of Halawa stream, Oahu. The structures of the new compounds were determined through the interpretation of spectral data. The absolute stereochemistries were determined using a combination of CD and NMR.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
