4741. HON

Nomenclature

CAS number: 26911-39-7; 4439-84-3 (unspecified stereo)
5-hydroxy-4-oxo-l-norvaline; l-2-amino-5-hydroxylevulinic acid; (S)-2-amino-4-oxo-5-hydroxypentanoic acid; δ-hydroxy-γ-oxo-l-norvaline.
C5H9NO4; mol wt 147.13.
C 40.82%, H 6.17%, N 9.52%, O 43.50%.

Description and references

Antitubercular antibiotic substance isolated from Streptomyces akiyoshiensis nova sp.: S. Tatsuoka et al., J. Antibiot. 14A, 39 (1961). Synthesis and structure: A. Miyake, Chem. Pharm. Bull. 8, 1071, 1074, 1079 (1960).

Chemical structure

Properties

Needles from water + acetone, no definite mp. [α]D20 6° (c = 1 in water); [α]D17 8.2° (c = 3.4 in water). pKa 2.91. uv max (water): 271 nm (ε 24). Stable in pure, dry state. Less stable in basic than in acidic solns. Colors red when heated in caustic soln, losing antibiotic activity. The dl-form is half as active as l-HON. LD50 in mice (mg/kg): 5200 i.v.; 8000 s.c.; 7600 orally (Tatsuoka).