400. Amidinomycin

Nomenclature

CAS number: 3572-60-9
(1R,3S)-3-Amino-N-(3-amino-3-iminopropyl)cyclopentanecarboxamide; ()-cis-N-(2-amidinoethyl)-3-aminocyclopentanecarboxamide; myxoviromycin.
C9H18N4O; mol wt 198.27.
C 54.52%, H 9.15%, N 28.26%, O 8.07%.

Description and references

Antiviral antibiotic produced by Streptomyces flavochromogenes isolated from Japanese soil (Shiuoka Prefecture). Isoln and structure: S. Nakamura et al., J. Antibiot. 14A, 103 (1961); S. Nakamura, Chem. Pharm. Bull. 9, 641 (1961). Identity with myxoviromycin: S. Nakamura et al., J. Antibiot. 14A, 163 (1961). Synthesis of (±)-cis and trans forms: H. Paul et al., Arch. Pharm. 301, 512 (1968). Crystal structure and absolute configuration: M. Kaneda et al., J. Antibiot. 33, 778 (1980). Enantioselective synthesis: H. Nagata et al., Tetrahedron: Asymmetry 8, 2679 (1997).

Chemical structure

Derivative

Sulfate.

Nomenclature

CAS number: 74984-58-0
C9H18N4O.H2SO4; mol wt 296.34.
C 36.48%, H 6.80%, N 18.91%, O 27.00%, S 10.82%.

Properties

Plates or needles from water + methanol, dec 285-288°. [α]D21 3.9° (c = 3). Absorption spectra: S. Nakamura, loc. cit. Soluble in water. Practically insol in ether, benzene, ethyl acetate, methanol, ethanol, butanol, acetone.