U. Zehavi, N. Sharon
Jan 25, 1973
Citations
0
Influential Citations
36
Citations
Journal
The Journal of biological chemistry
Abstract
Abstract N-Acetylbacillosamine, the 4-acetamido-2-amino-2,4,6-trideoxy-hexose isolated from a polysaccharide of Bacillus licheniformis (Sharon, N., and Jeanloz, R. W. (1960) J. Biol. Chem. 235, 1), was oxidized by a mixture of periodate and permanganate, and the product was hydrolyzed by acid to yield d-allothreonine. The d-allothreonine was identified by amino acid analysis, by paper chromatography, and by its susceptibility to oxidation with d-amino acid oxidase. This established that the diamino sugar belong to the d series and that the substituents on C-4 and C-5 are cis. To establish the configuration at C-2, N-acetylbacillosamine was reduced and dinitrophenylated to yield a 4-acetamido-2-(2,4-dinitrophenyl)amino-2,4,6-trideoxy-hexitol. Acid hydrolysis followed by periodate-permanganate oxidation afforded N-(2,4-dinitrophenyl)-l-serine identified by paper chromatography and by optical rotatory dispersion. The amino group at C-2 is thus on the right in the Fischer projection of the molecule. Examination of the nuclear magnetic resonance spectrum of the fully acetylated derivative, tetraacetylbacillosamine, revealed that the compound is in the C 1 conformation; that H-2, H-3, H-4 and H-5 are in trans diaxial positions; and that the acetoxy group at C-3 is equatorial. Our findings show that N-acetylbacillosamine belongs to the d-gluco series and has the structure of 4-acetamido-2-amino-2,4,6-trideoxy-d-glucose.