Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of α-Iduronidase, β-Glucuronidase and Heparanase.
MPS I
azasugars
glucuronidases
heparanases
iduronidases
inhibitors
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
14 02 2023
14 02 2023
Historique:
revised:
01
12
2022
received:
27
10
2022
pubmed:
2
12
2022
medline:
16
2
2023
entrez:
1
12
2022
Statut:
ppublish
Résumé
1-Azasugar analogues of l-iduronic acid (l-IdoA) and d-glucuronic acid (d-GlcA) and their corresponding enantiomers have been synthesized as potential pharmacological chaperones for mucopolysaccharidosis I (MPS I), a lysosomal storage disease caused by mutations in the gene encoding α-iduronidase (IDUA). The compounds were efficiently synthesized in nine or ten steps from d- or l-arabinose, and the structures were confirmed by X-ray crystallographic analysis of key intermediates. All compounds were inactive against IDUA, although l-IdoA-configured 8 moderately inhibited β-glucuronidase (β-GLU). The d-GlcA-configured 9 was a potent inhibitor of β-GLU and a moderate inhibitor of the endo-β-glucuronidase heparanase. Co-crystallization of 9 with heparanase revealed that the endocyclic nitrogen of 9 forms close interactions with both the catalytic acid and catalytic nucleophile.
Identifiants
pubmed: 36453606
doi: 10.1002/cbic.202200619
doi:
Substances chimiques
Iduronidase
EC 3.2.1.76
heparanase
EC 3.2.1.-
Uronic Acids
0
Glucuronidase
EC 3.2.1.31
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200619Informations de copyright
© 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH.
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