Methylenomycin A

Methylenomycin A

Names
IUPAC name (1S,2R,5S)-1,5-dimethyl-3-methylidene-4-oxo-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid
Identifiers
CAS Number	52775-76-5
3D model (Jmol)	Interactive image
ChemSpider	9074545
PubChem	10899285
InChI 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 Key: HBECYYFDLZZMPL-WLGLDCGKSA-N 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
SMILES O=C1C(=C)[C@@H](C(=O)O)[C@@]2(O[C@]12C)C
Properties
Chemical formula	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).
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Infobox references

Methylenomycin A is a cyclopentanoid 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.

See also

• Methylenomycin B

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. 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. PMC 206543. PMID 1537793.