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N-Alkyl derivatives of 2-amino-2-deoxy-D-glucose
Authors:Liberek Beata  Melcer Anna  Osuch Anna  Wakieć Roland  Milewski Sławomir  Wiśniewski Andrzej
Affiliation:Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chemik.chem.univ.gda.pl
Abstract:Mono- and di-N-alkylated derivatives of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucose (alkyl=methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl) were synthesised by the reductive alkylation of per-O-acetyl-d-glucosamine. (N-ethyl, N-propyl, N-butyl, N-pentyl and N-hexyl)-1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucoses were deacetylated in order to attempt an enzymatic phosphorylation. All products were characterised by means of IR, NMR and MS spectra. N-Ethyl- and N-pentyl-d-glucosamines were found to exhibit weak antifungal activity.
Keywords:  smallcaps"  >d-Glucosamine   Reductive alkylation   Deacetylation   NMR analysis   Enzymatic phosphorylation   Antifungal activity
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