Nanaomycin B
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| Category | Antibiotics |
| Catalog number | BBF-01981 |
| CAS | 52934-85-7 |
| Molecular Weight | 320.29 |
| Molecular Formula | C16H16O7 |
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Description
Nanaomycin B is an antibiotic produced by Str. rosa subsp. notoensis. It has anti-gram-positive bacteria, mycobacteria, mycoplasma and fungi activity.
Specification
| Synonyms | Antibiotic OS 3966B; 1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,4a,5,10,10a-hexahydro-9,10a-dihydroxy-1-methyl-5,10-dioxo-, (1S-(1-alpha,3-beta,4a-alpha,10a-beta))- |
| Storage | Store at -20°C |
| IUPAC Name | 2-[(3R,10aR)-9,10a-dihydroxy-1-methyl-5,10-dioxo-1,3,4,4a-tetrahydrobenzo[g]isochromen-3-yl]acetic acid |
| Canonical SMILES | CC1C2(C(CC(O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O)O |
| InChI | InChI=1S/C16H16O7/c1-7-16(22)10(5-8(23-7)6-12(18)19)14(20)9-3-2-4-11(17)13(9)15(16)21/h2-4,7-8,10,17,22H,5-6H2,1H3,(H,18,19)/t7?,8-,10?,16+/m1/s1 |
| InChI Key | IRFITFGOKXSNHV-GHYDZUPMSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma; mycobacteria |
| Boiling Point | 643.7°C at 760 mmHg |
| Melting Point | 84-86°C |
| Density | 1.492 g/cm3 |
| Solubility | Soluble in Methanol, Ether |
Reference Reading
1. New compounds, nanaomycin F and G, discovered by physicochemical screening from a culture broth of Streptomyces rosa subsp. notoensis OS-3966
Takuji Nakashima, Panitch Boonsnongcheep, Toru Kimura, Masato Iwatsuki, Noriko Sato, Kenichi Nonaka, Sompop Prathanturarug, Yōko Takahashi, Satoshi Ōmura J Biosci Bioeng. 2015 Nov;120(5):596-600. doi: 10.1016/j.jbiosc.2015.03.018. Epub 2015 Jun 20.
Two new compounds, nanaomycin F and G, were isolated by physicochemical screening method from cultured broth of Streptomyces rosa subsp. notoensis OS-3966, which is known to produce nanaomycin A, B, C, D, and E. Nanaomycin F is a new nanaomycin analog, a 4a-hydroxyl analog of nanaomycin B. Nanaomycin G has a unique skeleton with 1-indanone infused with a tetrahydropyran ring. Nanaomycin A possesses broad antimicrobial activity but nanaomycin F and G demonstrated no bioactivity against all bacteria and fungi tested in this study. In addition, in both nanaomycin F and G, the production of superoxide radicals was majorly decreased in comparison to nanaomycin A. It was considered that the antimicrobial properties were lost as a result of the decrease in production of the superoxide radicals.
2. Bioconversion and biosynthesis of nanaomycins using cerulenin, a specific inhibitor of fatty acid and polyketide biosyntheses
C Kitao, H Tanaka, S Minami, S Omura J Antibiot (Tokyo). 1980 Jul;33(7):711-6. doi: 10.7164/antibiotics.33.711.
The biosynthetic relationship of the nanaomycins produced by Streptomyces rosa var. notoensis OS-3966 was studied by means of a bioconversion method using the antibiotic cerulenin, a specific inhibitor of fatty acid and polyketide biosyntheses. Nanaomycin D was considered to be the first component produced from the hypothetical intermediate "polyketide". It is proposed that the biosynthesis sequence for the nanaomycin is: nanaomycin D leads to nanaomycin A leads to nanaomycin E leads to nanaomycin B. Nanaomycin B can be converted to nanaomycin A by non-enzymatic dehydration; however, nanaomycin A is rapidly bioconverted to nanaomycin E, which is the major component synthesized by the nanaomycin-producing strain.
3. Biosynthesis of nanaomycin: syntheses of nanaomycin E from nanaomycin A and of nanaomycin B from nanaomycin E in a cell-free system
S Omura, S Minami, H Tanaka J Biochem. 1981 Jul;90(1):291-3. doi: 10.1093/oxfordjournals.jbchem.a133465.
The enzyme reactions from NNM-A to NNM-E and from NNM-E to NNM-B were established in a cell-free system containing an extract from the nanaomycin producer Streptomyces rosa var. notoensis. The enzyme which catalyses the former epoxide-forming reaction (NNM-A leads to NNM-E) required NADH (or NADPH) and O2 suggesting that it is the monooxygenase-type; thus, NNM-A monooxygenase (4a,10a-epoxidizing) is proposed as its name. The other enzyme which catalyses the reductive epoxide-opening reaction (NNM-E leads to NNM-B) requires NADH or NADPH and is tentatively named NNM-B synthetase. Such a reductive epoxide-opening reaction is a novel enzyme reaction.
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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 ╳
