Anisomycin

Anisomycin[1]
Names
Preferred IUPAC name
(2R,3S,4S)-4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
Other names
Flagecidin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.041.139 Edit this at Wikidata
UNII
  • InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m0/s1 checkY
    Key: YKJYKKNCCRKFSL-BFHYXJOUSA-N checkY
  • InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m0/s1
    Key: YKJYKKNCCRKFSL-BFHYXJOUBQ
  • O=C(O[C@@H]1[C@@H](NC[C@H]1O)Cc2ccc(OC)cc2)C
Properties
C14H19NO4
Molar mass 265.309 g·mol−1
Melting point 139 to 143 °C (282 to 289 °F; 412 to 416 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Anisomycin, also known as flagecidin, is an antibiotic produced by Streptomyces griseolus which inhibits eukaryotic protein synthesis. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis.[2] Anisomycin can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways.

  1. ^ Anisomycin Archived January 19, 2012, at the Wayback Machine from Sigma Aldrich
  2. ^ Grollman, Arthur P. (1967). "Inhibitors of protein biosynthesis. II. Mode of action of anisomycin". The Journal of Biological Chemistry. 242 (13): 3226–33. doi:10.1016/S0021-9258(18)95953-3. PMID 6027796.