Aureothin
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| Category | Antibiotics |
| Catalog number | BBF-00609 |
| CAS | 2825-00-5 |
| Molecular Weight | 397.42 |
| Molecular Formula | C22H23NO6 |
| Purity | >95% by HPLC |
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Description
Aureothin is produced by the strain of Streptomyces thioluteus 4-A-1 and Streptomyces sp. 58. An unusual pyranone metabolite; has broad biological actions including antitumour, antimicrobial and insecticidal activities; a potent inhibitor of helicobacter pylori.
Specification
| Synonyms | Distacin; Mycolutein |
| Storage | -20°C |
| IUPAC Name | 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one |
| Canonical SMILES | CC1=C(OC(=C(C1=O)C)OC)C2CC(=CC(=CC3=CC=C(C=C3)[N+](=O)[O-])C)CO2 |
| InChI | InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1 |
| InChI Key | GQKXCBCSVYJUMI-WACKOAQBSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Pale Yellow Solid |
| Antibiotic Activity Spectrum | tumor; fungi; parasites |
| Melting Point | 156-157 °C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Interchenar retrotransfer of aureothin intermediates in an iterative polyketide synthase module
Christian Hertweck, Benjamin Busch, Yuki Sugimoto, Nico Ueberschaar J Am Chem Soc . 2012 Aug 1;134(30):12382-5. doi: 10.1021/ja304454r.
The course of the enigmatic iterative use of a polyketide synthase module was deduced from targeted domain inactivation in the aureothin assembly line. Mutational analyses revealed that the N-terminus of AurA is not involved in the iteration process, ruling out an ACP-ACP shuttle. Furthermore, an AurA(KS°, ACP°)-AurA(AT(0)) heterodimer proved to be nonfunctional, whereas aureothin production was restored in a ΔaurA mutant complemented with AurA(KS°)-AurA(ACP°). This finding supports a model according to which the ACP-bound polyketide intermediate is transferred back to the KS domain on the opposite PKS strand.
2. Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent
Alexandre Jean, Philippe A Peixoto, Jacques Maddaluno, Matthias Henrot, Michaël De Paolis J Org Chem . 2016 Jun 17;81(12):5190-201. doi: 10.1021/acs.joc.6b00878.
Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α'-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.
3. Exploiting enzymatic promiscuity to engineer a focused library of highly selective antifungal and antiproliferative aureothin analogues
Martin Roth, Longkuan Xiang, Jing He, Hans-Martin Dahse, Christian Hertweck, Bradley S Moore, Benjamin Busch, Martina Werneburg, Martin E A Richter J Am Chem Soc . 2010 Aug 4;132(30):10407-13. doi: 10.1021/ja102751h.
Aureothin is a shikimate-polyketide hybrid metabolite from Streptomyces thioluteus with a rare nitroaryl moiety, a chiral tetrahydrofuran ring, and an O-methylated pyrone ring. The antimicrobial and antitumor activities of aureothin have caught our interest in modulating its structure as well as its bioactivity profile. In an integrated approach using mutasynthesis, biotransformation, and combinatorial biosynthesis, a defined library of aureothin analogues was generated. The promiscuity of the polyketide synthase assembly line toward different starter units and the plasticity of the pyrone and tetrahydrofuran ring formation were exploited. A selection of 15 new aureothin analogues with modifications at the aryl residue, the pyrone ring, and the oxygenated backbone was produced on a preparative scale and fully characterized. Remarkably, various new aureothin derivatives are less cytotoxic than aureothin but have improved antiproliferative activities. Furthermore, we found that the THF ring is crucial for the remarkably selective activity of aureothin analogues against certain pathogenic fungi.
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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 ╳
