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
  • 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).
Infobox references

Elaiomycin is an antimicrobial chemical compound, classified as an azoxyalkene, 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]

Related Research Articles

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<i>Streptomyces</i> Genus of bacteria

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Bicyclomycin

Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteus that was isolated from Streptomyces sapporonesis and Streptomyces aizumenses in 1972. It belongs to a class of naturally occurring 2,5-diketopiperazines, that are among the most numerous of all the naturally occurring peptide antibiotics. This clinically useful antibiotic is rapidly absorbed in humans when given intramuscularly, has low toxicity and has been used to treat diarrhea in humans and bacterial diarrhea in calves and pigs.

Arylomycin

The arylomycins are a class of antibiotics initially isolated from a soil sample obtained in Cape Coast, Ghana. In this initial isolation, two families of closely related arylomycins, A and B, were identified. The family of glycosylated arylomycin C lipopeptides were subsequently isolated from a Streptomyces culture in a screen for inhibitors of bacterial signal peptidase. The initially isolated arylomycins have a limited spectrum of activity against Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pneumoniae. The only activity against Gram-negative bacteria was seen in strains with a compromised outer membrane.

Sangivamycin

Sangivamycin is a natural product originally isolated from Streptomyces rimosus, which is a nucleoside analogue. It acts as an inhibitor of protein kinase C. It has antibiotic, antiviral and anti-cancer properties and has been investigated for various medical applications, though never approved for clinical use itself. However, a number of related derivatives continue to be researched.

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.