Anisomycin

Title: Anisomycin
CAS Registry Number: 22862-76-6
CAS Name: (2R,3S,4S)-2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate
Additional Names: [2R-(2a,3a,4b)]-2-[(4-methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate; 2-p-methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine; 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-D-xylo-pentitol 3-acetate
Molecular Formula: C14H19NO4
Molecular Weight: 265.30
Percent Composition: C 63.38%, H 7.22%, N 5.28%, O 24.12%
Literature References: Protein synthesis inhibiting antibiotic isolated from Streptomyces: B. A. Sobin, F. W. Tanner, Jr., J. Am. Chem. Soc. 76, 4053 (1954); Tanner et al., US 2691618 (1954 to Pfizer). Activity: J. E. Lynch et al., Antibiot. Chemother. 4, 844, 899 (1954). Structure and stereochemistry: J. J. Beereboom et al., J. Org. Chem. 30, 2334 (1965); J. P. Schaefer, P. J. Wheatley, ibid. 33, 166 (1968); K. Butler, ibid. 2136. Biosynthesis: idem, ibid. 31, 317 (1966). Total synthesis: Oida, Ohki, Chem. Pharm. Bull. 16, 2086 (1968); ibid. 17, 1405 (1969); I. Felner, K. Schenker, Helv. Chim. Acta 53, 754 (1970). Chiral synthesis: J. P. H. Verheyden et al., Pure Appl. Chem. 50, 1363 (1978). Stereospecific total synthesis: D. P. Schumacher, S. S. Hall, J. Am. Chem. Soc. 104, 6076 (1982). Improved synthesis: A. N. Hulme, E. M. Rosser, Org. Lett. 4, 265 (2002). Mechanism of action: A. Jiménez, D. Vázquez in Antibiotics vol. 5(pt. 2), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 1-19. Soly and stability data: Antibiot. Annu. 1954-55, pp 809-810. Memory impairment effects in mice: K. M. Lattal, T. Abel, Proc. Natl. Acad. Sci. USA 101, 4667 (2004).
Properties: Long needles from ethyl acetate or water, mp 140-141°. [a]D23 -30° (methanol). uv max: 224, 277, 283 nm (e 10800, 1800, 1600). pKa 7.9. Base is moderately sol in water; sol in lower alcohols, esters, ketones, chloroform; slightly sol in benzene, toluene and hexane.
Melting point: mp 140-141°
pKa: pKa 7.9
Optical Rotation: [a]D23 -30° (methanol)
Absorption maximum: uv max: 224, 277, 283 nm (e 10800, 1800, 1600)
Derivative Type: Hydrochloride
CAS Registry Number: 1963-48-0
Molecular Formula: C14H19NO4.HCl
Molecular Weight: 301.77
Percent Composition: C 55.72%, H 6.68%, N 4.64%, O 21.21%, Cl 11.75%
Properties: Crystals from ethyl acetate + ethanol, mp 187-188°. Very sol in water.
Melting point: mp 187-188°
Derivative Type: Deacetylanisomycin
CAS Registry Number: 27958-06-1
Molecular Formula: C12H17NO3
Molecular Weight: 223.27
Percent Composition: C 64.55%, H 7.67%, N 6.27%, O 21.50%
Literature References: Prepn from anisomycin: Nickell et al., US 2935444 (1960 to Pfizer).
Properties: mp 176-179°. [a]D25 -20.0° (methanol), pK 9.2.
Melting point: mp 176-179°
pKa: pK 9.2
Optical Rotation: [a]D25 -20.0° (methanol)
Use: Agricultural fungicide.
Anisotropine Methylbromide Anistreplase Annatto Annexins Annotinine

Anisomycin[1]
Anisomycin structure.png
Identifiers
CAS number 22862-76-6 N
PubChem 31549
ChemSpider 29260 YesY
UNII 6C74YM2NGI YesY
ChEMBL CHEMBL423192 N
Jmol-3D images Image 1
Properties
Molecular formula C14H19NO4
Molar mass 265.31 g/mol
Melting point 139-143 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anisomycin, also known as flagecidin is an antibiotic produced by Streptomyces griseolus which inhibits 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.

Anisomycin is inactive against bacteria.