The Structure of Amicetin

The Journal of Organic Chemistry
1962.0

Abstract

A preliminary communication from our group assigned a tentative structural formula for amicetin. After a more detailed study, made possible especially by the availability of a larger quantity of the antibiotic, this structure assignment has been revised and evidence is presented in this paper that amicetin is better represented as I. Methanolysis of amicetin (I) yielded, besides cytimidine (II), the methyl glycosides (VI) of a neutral sugar, amicetose (VII), and of an amino sugar, amosamine (IX). Periodate fission of the 2,4-dinitrophenylhydrazone of amicetose (VIII) gave acetaldehyde and a derivative of succindialdehyde, leading to structure VII for the neutral sugar. Various degradations of amosamine and its derivatives were conducted and the results showed the amino sugar to be IX. Evidence is presented for the mode of linkage of amosamine, amicetose, and cytimidine in amicetin shown in structure I.

Knowledge Graph

Similar Paper

The Structure of Amicetin
The Journal of Organic Chemistry 1962.0
OXAMICETIN, A NEW ANTIBIOTIC OF BACTERIAL ORIGIN
The Journal of Antibiotics 1973.0
Hygromycin. III. Structure Studies
Journal of the American Chemical Society 1957.0
The Isolation and Characterization of Three Crystalline Antibiotics from Streptomyces plicatus
Journal of the American Chemical Society 1958.0
Apramycin, a unique aminocyclitol antibiotic
The Journal of Organic Chemistry 1976.0
Fortimicins A and B, new aminoglycoside antibiotics. III. Structural identification.
The Journal of Antibiotics 1977.0
Celesticetin. V. Structure of celesticetin
Journal of the American Chemical Society 1968.0
Structural elucidation of tunicamycin. II. The structure of tunicamycin.
Agricultural and Biological Chemistry 1977.0
Structure of Amidinomycin.
Chemical and Pharmaceutical Bulletin 1961.0
The structure of rimocidin.
The Journal of Antibiotics 1976.0