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一种在1,6位带有脒基的异法戈明类似物。

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

作者信息

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

机构信息

Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway.

Norwegian Biopolymer Laboratory (NOBIPOL), Department of Biotechnology and Food Science, NTNU Norwegian University of Science and Technology, Trondheim, Norway.

出版信息

R Soc Open Sci. 2025 Feb 19;12(2):241877. doi: 10.1098/rsos.241877. eCollection 2025 Feb.

DOI:10.1098/rsos.241877
PMID:39975658
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11836537/
Abstract

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 (IC > 50 µM against all tested enzymes) compared with isofagomine.

摘要

描述了一种在1,6位带有脒基的异法戈明类似物的合成。密度泛函理论计算表明，该化合物与异法戈明相比具有显著不同的电荷分布。这可能解释了为什么与异法戈明相比，脒是一种较差的糖苷酶抑制剂（对所有测试酶的IC>50µM）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/09d6b0891e7e/rsos.241877.f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/51cce5426287/rsos.241877.f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/169ea2543f46/rsos.241877.f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/0cfa0d23ed20/rsos.241877.f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/09d6b0891e7e/rsos.241877.f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/51cce5426287/rsos.241877.f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/169ea2543f46/rsos.241877.f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/0cfa0d23ed20/rsos.241877.f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9944/11836537/09d6b0891e7e/rsos.241877.f003.jpg

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J Med Chem. 2023 Feb 23;66(4):2744-2760. doi: 10.1021/acs.jmedchem.2c01750. Epub 2023 Feb 10.
2
Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of α-Iduronidase, β-Glucuronidase and Heparanase.尿嘧啶糖 1-氮杂糖的合成作为 α-艾杜糖醛酸酶、β-葡萄糖醛酸酶和硫酸乙酰肝素酶的潜在抑制剂。
Chembiochem. 2023 Feb 14;24(4):e202200619. doi: 10.1002/cbic.202200619. Epub 2023 Jan 3.
3
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Bioorg Chem. 2019 Jun;87:534-549. doi: 10.1016/j.bioorg.2019.03.053. Epub 2019 Mar 22.
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