4851. Hygromycin

Nomenclature

CAS number: 6379-56-2
(E)-5-Deoxy-5-[[3-[4-[(6-deoxy-β-d-arabino-hexofuranos-5-ulos-1-yl)oxy]-3-hydroxyphenyl]-2-methyl-1-oxo-2-propenyl]amino]-1,2-O-methylene-d-neo-inositol; homomycin; hygromycin A; 1703-18B; ST-4331.
C23H29NO12; mol wt 511.48.
C 54.01%, H 5.71%, N 2.74%, O 37.54%.

Description and references

Antibiotic substance produced by Streptomyces hygroscopicus (Jensen) Waksman & Henrici, from forest soil near Indianapolis, Ind: R. L. Mann et al., Antibiot. Chemother. 3, 1279 (1953). Produced also by Streptomyces noboritoensis from soil collected in Kanawaga Prefecture. Identity of homomycin and hygromycin: K. Isono et al., J. Antibiot. 10A, 21 (1957). Structure: eidem, ibid. 160; R. L. Mann, D. O. Woolf, J. Am. Chem. Soc. 79, 120 (1957). Abs config: K. Kakinuma, Y. Sakagami, Agric. Biol. Chem. 42, 279 (1978). Synthesis of the sugar component: M. Nakajima, S. Takahashi, ibid. 31, 1082 (1967). Total synthesis: N. Chida et al., Chem. Commun. 1989, 436. Peptide synthesis inhibitor: M. Guerrero, J. Modolell, Eur. J. Biochem. 107, 409 (1980).

Chemical structure

Properties

Amorphous white powder. mp 105-109°, dec above 160°. Also reported as mp 110-112° (dec) (Chida). Weakly acidic. pKa 8.9. [α]D25 126° (c = 1 in water). Freely sol in water, alc. Practically insol in the less polar solvents. uv max (dil HCl): 272, 214 nm (E1%1cm 306, 416).