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Synthesis 2022; 54(12): 2916-2926
DOI: 10.1055/a-1764-8950
DOI: 10.1055/a-1764-8950
paper
Functionalized d- and l-Arabino-Pyrrolidines as Potent and Selective Glycosidase Inhibitors
The authors acknowledge the ToppForsk program at the Universitetet i Stavanger (University of Stavanger) for financial support and the provision of a Ph.D. fellowship to M.B.H. (PR-10550). O.L. and J.G.F.B. are grateful to the Ministerio de Ciencia e Innovación funded by MCIN/AEI/10.13039/501100011033 (PID2020-116460RB-I00) and Junta de Andalucía (FQM-134).
Abstract
The 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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1764-8950.
- Supporting Information
Publication History
Received: 12 January 2022
Accepted after revision: 07 February 2022
Accepted Manuscript online:
07 February 2022
Article published online:
05 April 2022
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