Methylenomycin A

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.

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 ?)
Infobox references

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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