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Elaiomycin

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Elaiomycin
Names
IUPAC name (2S,3S)-(3-Hydroxy-1-methoxybutan-2-yl)imino--oxidoazanium
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
SMILES
  • CCCCCC/C=C\(=N\(COC)(C)O)\
Properties
Chemical formula C13H26N2O3
Molar mass 258.362 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Elaiomycin is an antimicrobial chemical compound, classified as an conjugated azoxyalkene, which was first isolated from Streptomyces in 1954. A laboratory synthesis of elaiomycin was reported in 1977.

A variety related compounds, collectively called elaiomycins, have also been reported.

References

  1. Haskell, Theodore H.; Ryder, Albert; Bartz, Quentin R. (1954). "Elaiomycin, a new tuberculostatic antibiotic; isolation and chemical characterization". Antibiotics & Chemotherapy (Northfield, Ill.). Antibiotics and Chemotherapy. 4 (2): 141–144. PMID 24542889.
  2. Erlich, J.; Anderson, LE; Coffey, GL; Feldman, WH; Fisher, MW; Hillegas, AB; Karlson, AG; Knudsen, MP; Weston, JK; Youmans, AS; Youmans, GP (1954). "Elaiomycin, a new tuberculostatic antibiotic; biologic studies". Antibiotics & Chemotherapy (Northfield, Ill.). Antibiotics and Chemotherapy. 4 (3): 338–342. PMID 24542957.
  3. Moss RA, Matsuo M (March 1977). "The synthesis of elaiomycin, a naturally occurring azoxyalkene". Journal of the American Chemical Society. 99 (5): 1643–5. doi:10.1021/ja00447a060. PMID 839012.
  4. Helaly, Soleiman E.; Pesic, Alexander; Fiedler, Hans-Peter; Süssmuth, Roderich D. (2011). "Elaiomycins B and C: Alkylhydrazide Antibiotics from Streptomyces sp. BK 190". Organic Letters. 13 (5): 1052–1055. doi:10.1021/ol1031014. PMID 21309518.
  5. Ding L, Ndejouong Ble S, Maier A, Fiebig HH, Hertweck C (October 2012). "Elaiomycins D-F, antimicrobial and cytotoxic azoxides from Streptomyces sp. strain HKI0708". Journal of Natural Products. 75 (10): 1729–34. doi:10.1021/np300329m. PMID 23013356.


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