Methylenomycin A

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Methylenomycin A
Methylenomycin A.svg
Methylenomycin A 3D ball.png
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
PubChem CID
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 Yes check.svgY
    Key: HBECYYFDLZZMPL-WLGLDCGKSA-N Yes check.svgY
  • 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 182.175 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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] The last step of its biosynthesis is epoxidation of the alkene of methylenomycin C. [3]

Biosynthesis of methylenomycin A Premethylenomycin C lactone metabolism.svg
Biosynthesis of methylenomycin A

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". Journal of Bacteriology. 178 (11): 3221–3231. doi:10.1128/jb.178.11.3221-3231.1996. PMC   178074 . PMID   8655502.
  2. ↑ Hobbs G, Obanye AI, Petty J, Mason JC, Barratt E, Gardner DC, et al. (March 1992). "An integrated approach to studying regulation of production of the antibiotic methylenomycin by Streptomyces coelicolor A3(2)". Journal of Bacteriology. 174 (5): 1487–1494. doi:10.1128/jb.174.5.1487-1494.1992. PMC   206543 . PMID   1537793.
  3. ↑ Corre C, Idowu GA, Song L, Whitehead ME, Alkhalaf LM, Challis GL (November 2025). "Discovery of Late Intermediates in Methylenomycin Biosynthesis Active against Drug-Resistant Gram-Positive Bacterial Pathogens". Journal of the American Chemical Society. 147 (44): 40554–40561. doi:10.1021/jacs.5c12501. PMC   12593393 . PMID   41145303.
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