Methylenomycin A

Methylenomycin A

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^Y
PubChem	10899285
ChemSpider	9074545^Y
Jmol-3D images	Image 1
SMILES O=C1C(=C)[C@@H](C(=O)O)[C@@]2(O[C@]12C)C
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^Y Key: HBECYYFDLZZMPL-WLGLDCGKSA-N^Y 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
Properties
Molecular formula	C₉H₁₀O₄
Molar mass	182.19 g mol^-1
Boiling point	341.2 °C
Hazards
Flash point	141.2 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

References

^ 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. http://jb.asm.org/cgi/pmidlookup?view=long&pmid=8655502.
^ 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. http://jb.asm.org/cgi/pmidlookup?view=long&pmid=1537793.

Methylenomycin A

See also

References