An isofagomine analogue with an amidine group in the 1,6-position

I. Caroline Vaaland Holmgard; Idd Andrea Christensen; Ljupcho Pejov; Monika Moreń; Nikolai Westlund; Tereza Cristina Santos Evangelista; Magne O. Sydnes; Finn L. Aachmann; Óscar López; Emil Lindbäck

doi:10.1098/rsos.241877

Royal Society Open Science (Feb 2025)

An isofagomine analogue with an amidine group in the 1,6-position

I. Caroline Vaaland Holmgard,
Idd Andrea Christensen,
Ljupcho Pejov,
Monika Moreń,
Nikolai Westlund,
Tereza Cristina Santos Evangelista,
Magne O. Sydnes,
Finn L. Aachmann,
Óscar López,
Emil Lindbäck

Affiliations

I. Caroline Vaaland Holmgard: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
Idd Andrea Christensen: Norwegian Biopolymer Laboratory (NOBIPOL), Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Trondheim, Norway
Ljupcho Pejov: Institute of Chemistry, Faculty of Natural Sciences and Mathematics, SS Cyril and Methodius University, Skopje, North Macedonia
Monika Moreń: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
Nikolai Westlund: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
Tereza Cristina Santos Evangelista: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
Magne O. Sydnes: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
Finn L. Aachmann: Norwegian Biopolymer Laboratory (NOBIPOL), Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Trondheim, Norway
Óscar López: Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Seville, Spain
Emil Lindbäck: Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway

DOI: https://doi.org/10.1098/rsos.241877
Journal volume & issue: Vol. 12, no. 2

Abstract

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The synthesis of an isofagomine analogue with an amidine group in the 1,6-position is described. Density functional theory calculations showed that this compound has a remarkably different charge distribution compared with isofagomine. This may explain why the amidine is a poor glycosidase inhibitor (IC50 > 50 µM against all tested enzymes) compared with isofagomine.

Published in Royal Society Open Science

ISSN: 2054-5703 (Online)
Publisher: The Royal Society
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://royalsocietypublishing.org/journal/rsos

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