92447-09-1Relevant articles and documents
The Deamination of 1-Aminohexan-2-ol and 1-(Aminomethyl)pentyl β-D-Galactopyranoside; a Model Study of the Selective Cleavage of the Hydroxylysine-bound Glycosyl Residues of Collagen
Tang, Ping W.,Williams, J. Michael
, p. 1199 - 1204 (2007/10/02)
The reaction of 1-aminohexan-2-ol with nitrous acid gave a mixture of hexan-2-one, hexan-1,2-diol, 5-butyl-N-nitroso-2-pentyloxazolidine and 2,5-dibutyl-2-methyl-N-nitroso-oxazolidine, the proportions of which varied with the reaction conditions.The absence of 1,2-epoxyhexane from the product mixture is in marked contrast to results recently reported for a related aminoalcohol. 1-(Aminomethyl)pentyl β-D-galactopyranoside was synthesized as a model compound for the O-glycosylhydroxylysine residues of collagen, by the Lewis acid-catalysed reaction of β-D-galactopyranose penta-acetate with 1-nitrohexan-2-ol followed by reduction and deacetylation.The nitrosation of 1-(aminomethyl)pentyl β-D-galactopyranoside at pH 3.0-3.5 gave, as major products (>90percent), D-galactose and hexan-2-one.This reaction constitutes a model for the selective cleavage, under very mild conditions, of the hydroxylysine-bound glycosyl residues of collagen.
