Hitachimycin

Discovery, producing organism and structure (1-3)

Hitachimycin is an antiprotozoal antibiotic isolated from the culture broth of the actinomycete strain KM-4927. Later, the antibiotic was found to be identical to an antitumor antibiotic, stubomycin (1). The relative and absolute stereochemistry was defined via NMR and X-ray crystallographic analyses (2,3). The total synthesis was reported by Smith et al (4,5).

Physical data

Colorless plates. C₂₉H₃₅NO₅; mol wt 477. Sol. in DMSO, pyridine, DMF, MeOH. Insol. in H₂O, CHCl₃, Et₂O.

Biological activity (2,4,5)

1) Antimicrobial activity (6)

2) Antitumor activity of hitachimycin and its derivatives (6-9)

References

1. [252] S. Ōmura et al., Tetrahedron Lett., 23, 4713-4716 (1982)
2. Umezawa et al., J. Antibiot., 34, 259 (1981)
3. [435] A. B. Smith, III et al., J. Org. Chem., 55, 1133-1135 (1990)
4. [489] A. B. Smith, III et al., J. Am. Chem. Soc., 114, 8003-8007 (1992)
5. A.B. Smith, III et al. J. Org. Chem. 55, 1136 (1990).