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. |