208. Alazopeptin

Nomenclature

CAS number: 1397-84-8
l-Alanyl-(6-diazo-5-oxo)-l-norleucyl-(6-diazo-5-oxo)-l-norleucine.
C15H20N6O5; mol wt 364.36.
C 49.45%, H 5.53%, N 23.07%, O 21.96%.

Description and references

Tumor-inhibiting antibiotic produced by Streptomyces griseoplanus from soil near Williamsburg, Iowa: De Voe et al., Antibiot. Annu. 1956-7, p 730. Peptide consisting of one mole α-alanine and two moles of a C6 diazo keto amino acid oxidizable to glutamic acid: E. L. Patterson et al., Antimicrob. Agents Chemother. 1965, 115-118. Anti-tumor activity: T. Hata et al., J. Antibiot. 26, 181 (1973). Toxicity: J. B. Thiersch, Proc. Soc. Exp. Biol. Med. 97, 888 (1958).

Chemical structure

Derivative

Monohydrate.

Properties

Crystals from dilute acetone. Poor stability. Has no definite melting point. [α]D25 +9.5° (c = 4.7 in H2O). uv max (pH 7.0 phosphate buffer): 242, 274 nm (E1%1cm 321, 549). Freely sol in water. Somewhat sol in acetic acid, formamide, DMSO, aq solns of methanol, ethanol, acetone. Practically insol in anhydr alcohols, acetone, ethyl acetate, ether. LD50 i.p. in rats: 150 mg/kg (Thiersch).