N-Alkyl derivatives of 2-amino-2-deoxy-d-glucose

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• 作者：Beata Liberek ; Anna Melcer ; Anna Osuch ; Roland Wakieć ; Sł ; awomir Milewski and Andrzej Wiś ; niewski
• 关键词：d-Glucosamine ; Reductive alkylation ; Deacetylation ; NMR analysis ; Enzymatic phosphorylation ; Antifungal activity
• 刊名：Carbohydrate Research
• 出版年：2005
• 期刊代码：15_00086215
• 类别：ch
• 出版时间：2005
• 卷：340
• 期：11
• 页码：1876-1884
• 文件大小：159 K

摘要

Mono- and di-N-alkylated derivatives of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-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-β-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.