Methylenomycin A

Methylenomycin A
Structural formula of methylenomycin A
Ball-and-stick model of the methylenomycin A molecule
Names
Preferred IUPAC name
(1S,2R,5S)-1,5-Dimethyl-3-methylidene-4-oxo-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C9H10O4/c1-4-5(7(11)12)8(2)9(3,13-8)6(4)10/h5H,1H2,2-3H3,(H,11,12)/t5-,8-,9+/m0/s1 checkY
    Key: HBECYYFDLZZMPL-WLGLDCGKSA-N checkY
  • InChI=1/C9H10O4/c1-4-5(7(11)12)8(2)9(3,13-8)6(4)10/h5H,1H2,2-3H3,(H,11,12)/t5-,8-,9+/m0/s1
    Key: HBECYYFDLZZMPL-WLGLDCGKBO
  • O=C1C(=C)[C@@H](C(=O)O)[C@@]2(O[C@]12C)C
Properties
C9H10O4
Molar mass 182.19 g mol−1
Boiling point 341.2 °C (646.2 °F; 614.3 K)
Hazards
Flash point 141.2 °C (286.2 °F; 414.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Methylenomycin A is a cyclopentanone derived antibiotic produced by Streptomyces coelicolor A3(2) that is effective against both Gram-negative and Gram-positive bacteria.[1][2] Methylenomycins are naturally produced in two variants: A and B.[citation needed]

See also

References

  1. ^ Brian P, Riggle PJ, Santos RA, Champness WC (June 1996). "Global negative regulation of Streptomyces coelicolor antibiotic synthesis mediated by an absA-encoded putative signal transduction system". J. Bacteriol. 178 (11): 3221–31. doi:10.1128/jb.178.11.3221-3231.1996. PMC 178074. PMID 8655502.
  2. ^ Hobbs G, Obanye AI, Petty J, et al. (March 1992). "An integrated approach to studying regulation of production of the antibiotic methylenomycin by Streptomyces coelicolor A3(2)". J. Bacteriol. 174 (5): 1487–94. doi:10.1128/jb.174.5.1487-1494.1992. PMC 206543. PMID 1537793.


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