Epoxyalkyl oligo-(1 leads to 4)- -D-glucosides as active-site-directed inhibitors of cellulases

N-Deacetylation of benzyl 2-acetamido-2-deoxy-6-O-α-D-mannopyranosyl-α-D-glucopyranoside (3) by alkaline hydrolysis, or hydrazinolysis in the presence of hydrazine sulphate, proceeds quantitatively to yield the amine 4. The mannosyl glycosidic linkage in 4 can be selectively hydrolysed by acid, whereas the 2-amino-2-deoxyhexosyl glycosidic linkage is selectively cleaved upon treatment with sodium nitrite in dilute acetic acid. Aspects of the selective cleavage of hexosaminoglycans are discussed.