6985. Pactamycin

Nomenclature

CAS number: 23668-11-3
2-Hydroxy-6-methylbenzoic acid [(1S,2R,3R,4S,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[[(dimethylamino)carbonyl]amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl ester; NSC-52947; U-15800.
C28H38N4O8; mol wt 558.62.
C 60.20%, H 6.86%, N 10.03%, O 22.91%.

Description and references

Antitumor antibiotic produced by Streptomyces pactum var pactum. Discovery and biological properties: Bhuyan et al., Antimicrob. Agents Chemother. 1961, 184. Isoln and characterization: Argoudelis et al., ibid. 191. Manuf: GB 980346 (1965 to Upjohn), C.A. 62, 11115f (1965). Structure: Wiley et al., J. Org. Chem. 35, 1420 (1970). Revised structure: D. J. Duchamp, Am. Crystallogr. Assn. (Winter Mtg., Albuquerque, 1972) p 23. Mechanism of action: T. A. Beerman et al., Adv. Enzyme Regul. 14, 207 (1976). 13C-NMR study: D. D. Weller et al., J. Antibiot. 30, 997 (1978). Biosynthesis: D. D. Weller, K. L. Rinehart, J. Am. Chem. Soc. 100, 6757 (1978). Review: Goldberg in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 498-515.

Chemical structure

Properties

[α]D25 +79° (ethanol) changing to +23° on standing. [α] changes in acetone on standing from +25° to +76° in 24 hours. Amphoteric. Sol in ethanol, chloroform, methylene chloride, benzene, ether, in solns <pH 5 and >9.5. Insol in Skellysolve B, cyclohexane; insol at isoelectric pt, pH 8.3. Unstable in solution. LD50 in mice (mg/kg): 10.7 orally; 15.6 i.v.; in rats (mg/kg): 1.4 i.v. (Bhuyan).