Elaiomycin

Elaiomycin
Names
	IUPAC name (2S,3S)-(3-Hydroxy-1-methoxybutan-2-yl)imino-[(E)-oct-1-enyl]-oxidoazanium
Identifiers
CAS Number	23315-05-1;
3D model (JSmol)	Interactive image;
ChemSpider	16735790;
PubChem CID	6141900;
UNII	227V1PL5TF;
	SMILES CCCCCC/C=C\[N+](=N\[C@@H](COC)[C@H](C)O)\[O-];
Properties
Chemical formula	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). Infobox references

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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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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