8800. Statine

Nomenclature

CAS number: 49642-07-1
(3S,4S)-4-Amino-3-hydroxy-6-methylheptanoic acid; AHMHA.
C8H17NO3; mol wt 175.23.
C 54.83%, H 9.78%, N 7.99%, O 27.39%.

Description and references

Amino acid present in pepstatin, q.v. Synthesis: H. Morishima et al., J. Antibiot. 26, 115 (1973). Abs config and stereospecific synthesis of all four isomers: M. Kinoshita et al., ibid. 249. Crystal structure: H. Nakamura et al., ibid. 255. Biosynthesis: H. Morishima et al., ibid. 27, 267 (1974). Alternate syntheses: M. Kinoshita et al., Bull. Chem. Soc. Jpn. 48, 570 (1975); W.-S. Liu, G. I. Glover, J. Org. Chem. 43, 754 (1978); D. H. Rich et al., ibid. 3624; K. E. Rittle et al., ibid. 47, 3016 (1982). Distribution in rats: D. A. Grant et al., Biochem. Pharmacol. 31, 2302 (1982).

Chemical structure

Properties

mp 201-203° (dec). [α]D15 20° (c = 0.64 in water).