Elaiomycin

Last updated
Elaiomycin
Elaiomycin.svg
Names
IUPAC name
(2S,3S)-(3-Hydroxy-1-methoxybutan-2-yl)imino-[(E)-oct-1-enyl]-oxidoazanium
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H26N2O3/c1-4-5-6-7-8-9-10-15(17)14-13(11-18-3)12(2)16/h9-10,12-13,16H,4-8,11H2,1-3H3/b10-9+,15-14?
    Key: BCPWSYQGYBTINM-HDHZNLKHSA-N
  • CCCCCC/C=C\[N+](=N\[C@@H](COC)[C@H](C)O)\[O-]
Properties
C13H26N2O3
Molar mass 258.362 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Elaiomycin is an antimicrobial chemical compound, classified as an conjugated azoxy alkene, which was first isolated from Streptomyces in 1954. [1] [2] A laboratory synthesis of elaiomycin was reported in 1977. [3]

A variety related compounds, collectively called elaiomycins, have also been reported. [4] [5]

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. Bibcode:1977JAChS..99.1643M. 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. Bibcode:2012JNAtP..75.1729D. doi:10.1021/np300329m. PMID   23013356.


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