12-00422. Amidomycin [Archived]

Nomenclature

CAS number: 552-33-0
C40H68N4O12; mol wt 796.99.
C 60.28%, H 8.60%, N 7.03%, O 24.09%.

Description and references

Antibiotic substance produced by an unidentified Streptomyces culture (PRL 1642). Composed of 4 moles each of d-()-valine and d-()-α-hydroxyisovaleric acid, linked alternately by ester and amide bonds to form a 24-membered ring: Vining, Taber, Can. J. Chem. 35, 1109 (1957). Structure studies: Shemyakin et al., Tetrahedron Lett. 1963, 351, Tetrahedron 19, 995 (1963).

Chemical structure

Properties

Needles from dilute ethanol or petr ether, mp 192°. [α]D26 +19.2° (c = 1.2 in ethanol). Neutral reaction. Practically insol in water. Readily sol in most organic solvents. Primarily active against yeasts.

Status

This monograph has been retired and is no longer subject to revision or update.