Affiliation:
1. Faculty of Science and Technology, Department of Chemistry, Bioscience, and Environmental Engineering, University of Stavanger
2. Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla
Abstract
AbstractThe efficient synthesis of enantiomeric pairs of iminosugars including 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) and 1,4-dideoxy-1,4-imino-l-arabinitol (LAB) analogues with an amidine, hydrazide, hydrazide imide, or amide oxime moiety is described. The preparation of DAB and LAB analogues commenced from l-xylose and d-xylose, respectively. The obtained iminosugars are tested against a panel of glycosidases with pharmaceutical relevance, revealing enhanced activity for the DAB analogues in comparison with the LAB analogues. In particular, the d-arabino-configured amidine behaved as a potent (submicromolar range) and selective inhibitor of α-mannosidase.
Funder
Universitetet i Stavanger
Ministerio de Ciencia e Innovación
Junta de Andalucía
Subject
Organic Chemistry,Catalysis
Cited by
2 articles.
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