N-Alkyl derivatives of 2-amino-2-deoxy-D-glucose.
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.
Liberek
Beata
B
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chemik.chem.univ.gda.pl
Melcer
Anna
A
Osuch
Anna
A
Wakieć
Roland
R
Milewski
Sławomir
S
Wiśniewski
Andrzej
A
D000935:Antifungal Agents / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003847:Deoxyglucose / Q000138:chemical synthesis / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010766:Phosphorylation; D011522:Protons; D013055:Spectrophotometry, Infrared; D013696:Temperature
D000935:Antifungal Agents; D011522:Protons; C035547:glucosaminic acid; D003847:Deoxyglucose; D005944:Glucosamine