Notonesomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02139 |
| CAS | 102525-63-3 |
| Molecular Weight | 1454.66 |
| Molecular Formula | C68H111NO30S |
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Description
Notonesomycin A is originally isolated from Str. aminophilus subsp. notonesogenes 647-AV1. It has the effect of resisting plant pathogenic bacteria and fungi, and its effect is similar to that of Validamycin.
Specification
| Synonyms | NSC608604 |
| IUPAC Name | 3-[[(17E)-14-[3,5-dihydroxy-7-[4-[3-(5-hydroxy-6-methyloxan-2-yl)oxy-4-(methylamino)benzoyl]oxy-5-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethylnonan-2-yl]-5,9,20,22,28,29,30,31-octahydroxy-13,27-dimethyl-16-oxo-32-sulfooxy-11,15,34-trioxatricyclo[28.3.1.010,12]tetratriacont-17-en-3-yl]oxy]-3-oxopropanoic acid |
| Canonical SMILES | CCC(C(C)C(C(C)C(C(C)C1C(C2C(O2)C(CCCC(CC(CC3CC(C(C(O3)(C(C(C(CCCCC(CC(CC=CC(=O)O1)O)O)C)O)O)O)O)OS(=O)(=O)O)OC(=O)CC(=O)O)O)O)C)O)O)OC4CC(C(C(O4)C)OC)OC(=O)C5=CC(=C(C=C5)NC)OC6CCC(C(O6)C)O |
| InChI | InChI=1S/C68H111NO30S/c1-11-49(93-57-31-51(63(89-10)39(8)91-57)95-67(84)40-22-23-46(69-9)50(26-40)94-56-25-24-47(73)38(7)90-56)34(3)59(80)35(4)60(81)36(5)61-37(6)62-64(97-62)48(74)20-14-18-43(72)28-44(92-55(78)32-53(75)76)29-45-30-52(99-100(86,87)88)65(82)68(85,98-45)66(83)58(79)33(2)16-12-13-17-41(70)27-42(71)19-15-21-54(77)96-61/h15,21-23,26,33-39,41-45,47-49,51-52,56-66,69-74,79-83,85H,11-14,16-20,24-25,27-32H2,1-10H3,(H,75,76)(H,86,87,88)/b21-15+ |
| InChI Key | HVHQPPAFOWCAJP-RCCKNPSSSA-N |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 194-195°C |
Reference Reading
1. A novel macrolide antibiotic, notonesomycin A
T Sasaki, K Furihata, A Shimazu, H Seto, M Iwata, T Watanabe, N Otake J Antibiot (Tokyo). 1986 Apr;39(4):502-9. doi: 10.7164/antibiotics.39.502.
Fermentation of Streptomyces aminophilus subsp. notonesogenes 647-AV1 produced a mixture of antifungal antibiotics. Notonesomycin A, the main component has been characterized as a new macrolide antibiotic containing a sulfate group, a malonate moiety, two deoxysugars and a 1,3,4-trisubstituted benzene system in the molecule. It was active against some fungi and Gram-positive bacteria in vitro and effective against the sheath blight disease of rice plant in a green house test.
2. Identification and engineering of 32 membered antifungal macrolactone notonesomycins
Falicia Goh, Mingzi M Zhang, Tian Ru Lim, Kia Ngee Low, et al. Microb Cell Fact. 2020 Mar 19;19(1):71. doi: 10.1186/s12934-020-01328-x.
Notonesomycin A is a 32-membered bioactive glycosylated macrolactone known to be produced by Streptomyces aminophilus subsp. notonesogenes 647-AV1 and S. aminophilus DSM 40186. In a high throughput antifungal screening campaign, we identified an alternative notonesomycin A producing strain, Streptomyces sp. A793, and its biosynthetic gene cluster. From this strain, we further characterized a new more potent antifungal non-sulfated analogue, named notonesomycin B. Through CRISPR-Cas9 engineering of the biosynthetic gene cluster, we were able to increase the production yield of notonesomycin B by up to 18-fold as well as generate a strain that exclusively produces this analogue.
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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 ╳
