Aureothin

Aureothin is a cytotoxic shikimate-polyketide antibiotic with the molecular formula C22H23NO6.[2][3][1] Aureothin is produced by the bacterium Streptomyces thioluteus.[3][4] new aureothin derivatives can be antifungal and antiproliferative.[2]

Aureothin
Names
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[1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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
    Key: GQKXCBCSVYJUMI-WACKOAQBSA-N
  • CC1=C(OC(=C(C1=O)C)OC)[C@H]2C/C(=C/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C)/CO2[1]
Properties
C22H23NO6
Molar mass 397.427 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Aureothin". Pubchem.
  2. Issues in Chemistry and General Chemical Research (2011 ed.). ScholarlyEditions. 9 January 2012. p. 442. ISBN 978-1-4649-6334-6.
  3. He, Jing; Hertweck, Christian (1 March 2004). "Biosynthetic Origin of the Rare Nitroaryl Moiety of the Polyketide Antibiotic Aureothin: Involvement of an Unprecedented N-Oxygenase". Journal of the American Chemical Society. 126 (12): 3694–3695. doi:10.1021/ja039328t.
  4. Hirata, Yoshimasa; Nakata, Hisao; Yamada, Kiyoyuki; Okuhara, Kunio; Naito, Takayuki (January 1961). "The structure of aureothin, a nitro compound obtained from Streptomyces thioluteus". Tetrahedron. 14 (3–4): 252–274. doi:10.1016/S0040-4020(01)92175-1.

Further reading
  • Natural Product Biosynthesis by Microorganisms and Plants Part C. Academic Press. 31 December 2012. p. 216. ISBN 978-0-12-404617-7.
  • Strategies and Tactics in Organic Synthesis. Elsevier. 4 October 2016. p. 120. ISBN 978-0-08-100762-4.
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