206. l-Alanosine

Nomenclature

CAS number: 5854-93-3
3-(Hydroxynitrosoamino)-l-alanine; l-2-amino-3-(hydroxynitrosoamino)propanoic acid; l-2-amino-3-[(N-nitroso)hydroxylamino]propionic acid.
C3H7N3O4; mol wt 149.11.
C 24.16%, H 4.73%, N 28.18%, O 42.92%.

Description and references

Antibiotic substance from the fermentation of Streptomyces alanosinicus n. sp. Prepn: NL 6509543; J. Thiemann, Y. S. K. Murthy, US 3676490 (1966, 1972 both to Lepetit). The first natural product found to have a N-nitrosohydroxylamino group on an aliphatic chain. Isoln and structure: Coronelli et al., Farmaco Ed. Sci. 21, 269 (1966). Characterization: Thiemann, Beretta, J. Antibiot. 19A, 155 (1966). Structure and synthesis of l-, d- and dl-forms: Lancini et al., Tetrahedron Lett. 1966, 1769; eidem, Farmaco Ed. Sci. 24, 169 (1969). Synthesis of l-form: Isowa et al., Bull. Chem. Soc. Jpn. 46, 1847 (1973). Improved synthesis of dl-form: Eaton et al., J. Med. Chem. 16, 289 (1973). Pharmacology: Murthy et al., Nature 211, 1198 (1966). Mode of action studies: Gale et al., Biochem. Pharmacol. 17, 363, 1823 (1968). Effect on insect growth: E. E. Kenaga, J. Econ. Entomol. 62, 1006 (1969); S. Matsumoto et al., Agric. Biol. Chem. 48, 827 (1984).

Chemical structure

Properties

Crystalline powder from slightly acidic water, dec 190°. [α]D +8°, 46°, 37.8° (in 1N HCl, 0.1N NaOH, water). uv max (0.1N HCl): 228 nm (E1%1cm 505); in 0.1N NaOH: 250 nm (E1%1cm 630). pKa 4.8. Slightly sol in water; practically insol in the common organic solvents. Sol in alkaline and acidic solns, from which it ppts by adjusting the pH between 4 and 6. LD50 in mice (mg/kg): 600 i.p.; 300 i.v. (Thiemann, Murthy).

Derivative

d-Form.

Properties

mp 183°. [α]D +45° (c = 0.5N in 1N HCl).

Use

Experimental insect reproduction inhibitor.