ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of the Inhibitors of Glycanases

T. Stach, M. Matulová, V. Farkaš, Z. Sulová, V. Pätoprstý, and K. Linek

Institute of Chemistry, Slovak Academy of Sciences, SK-842 38 Bratislava

Abstract: 2,3-Epoxypropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was obtained by oxidation of allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside; deacetylation of the former compound afforded 2,3-epoxypropylacetyl-β-D-glucopyranoside, Analogous oxidation and deacetylation of allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside produced 2,3-epoxypropyl 2,3,4,6-tetra- O-acetyl-β-D-glucopyranosyl-(1→4)-2,3,6-O-acetyl-β-D-glucopyranoside and 2,3-epoxypropyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside respectively. Structure, anomeric and absolute configuration of these substances were determined by ¹H and ¹³C NMR spectroscopic methods, and mass spectrometric methods. The deacetylated epoxyalkyl β-D-glycosides were effective as irreversible active-site directed inhibitors of β-glycosidase from sweet almonds.

Full paper in Portable Document Format: 533a218.pdf

Chemical Papers 53 (3) 218–223 (1999)