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Lactimidomycin

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Chemical compound
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Pharmaceutical compound
Lactimidomycin
Identifiers
IUPAC name
  • 4--4-oxooct-6-enyl]piperidine-2,6-dione
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC26H35NO6
Molar mass457.567 g·mol
3D model (JSmol)
SMILES
  • N2C(=O)CC(CC2=O)CC(O)CC(=O)C(C)\C=C(/C)\C1OC(=O)C=CCCC=CC=CC1C
InChI
  • InChI=1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4+,10-8-,11-9+,19-12+/t17-,18-,21+,26+/m0/s1
  • Key:OYOKHBHOTQDIPM-BRHOHSSQSA-N

Lactimidomycin is a glutarimide antibiotic derived from the bacteria Streptomyces amphibiosporus. It has antifungal, antiviral and anti-cancer properties, acting as a direct inhibitor of protein translation in ribosomes. Antiviral activity is seen against a variety of RNA viruses including flaviviruses such as dengue fever, Kunjin virus and Modoc virus, as well as vesicular stomatitis virus and poliovirus. As lactimidomycin is a natural product containing an unusual unsaturated 12-membered lactone ring, it has been the subject of numerous total synthesis approaches.

References

  1. Sugawara K, Nishiyama Y, Toda S, Komiyama N, Hatori M, Moriyama T, et al. (September 1992). "Lactimidomycin, a new glutarimide group antibiotic. Production, isolation, structure and biological activity". The Journal of Antibiotics. 45 (9): 1433–41. doi:10.7164/antibiotics.45.1433. PMID 1429229.
  2. Ju J, Seo JW, Her Y, Lim SK, Shen B (December 2007). "New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus". Organic Letters. 9 (25): 5183–6. doi:10.1021/ol702249g. PMID 17997563.
  3. Schneider-Poetsch T, Ju J, Eyler DE, Dang Y, Bhat S, Merrick WC, et al. (March 2010). "Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin". Nature Chemical Biology. 6 (3): 209–217. doi:10.1038/nchembio.304. PMC 2831214. PMID 20118940.
  4. Micoine K, Persich P, Llaveria J, Lam MH, Maderna A, Loganzo F, Fürstner A (June 2013). "Total syntheses and biological reassessment of lactimidomycin, isomigrastatin and congener glutarimide antibiotics". Chemistry: A European Journal. 19 (23): 7370–83. doi:10.1002/chem.201300393. PMID 23595541.
  5. Garreau de Loubresse N, Prokhorova I, Holtkamp W, Rodnina MV, Yusupova G, Yusupov M (September 2014). "Structural basis for the inhibition of the eukaryotic ribosome". Nature. 513 (7519): 517–22. Bibcode:2014Natur.513..517G. doi:10.1038/nature13737. hdl:11858/00-001M-0000-0023-EE38-0. PMID 25209664. S2CID 4460881.
  6. Carocci M, Yang PL (April 2016). "Lactimidomycin is a broad-spectrum inhibitor of dengue and other RNA viruses". Antiviral Research. 128: 57–62. doi:10.1016/j.antiviral.2016.02.005. PMC 4850914. PMID 26872864.
  7. Micoine K, Fürstner A (October 2010). "Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin". Journal of the American Chemical Society. 132 (40): 14064–6. doi:10.1021/ja107141p. PMID 20831202.
  8. Larsen BJ, Sun Z, Nagorny P (June 2013). "Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization". Organic Letters. 15 (12): 2998–3001. doi:10.1021/ol401186f. PMID 23731327.
  9. Nagasawa T, Kuwahara S (June 2013). "Formal total synthesis of lactimidomycin". Organic Letters. 15 (12): 3002–5. doi:10.1021/ol401214f. PMID 23731346.
  10. Larsen BJ, Sun Z, Lachacz E, Khomutnyk Y, Soellner MB, Nagorny P (December 2015). "Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues". Chemistry: A European Journal. 21 (52): 19159–67. doi:10.1002/chem.201503527. PMID 26577990.


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