Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of a-Iduronidase, b-Glucuronidase and Heparanase Article Swipe
Gareth G. Doherty
,
Geraldine Jia Ming Ler
,
Norbert Wimmer
,
Paul V. Bernhardt
,
Roger A. Ashmus
,
David J. Vocadlo
,
Zachary Armstrong
,
G.J. Davies
,
Marco Maccarana
,
Jin‐Ping Li
,
Yasmin Kayal
,
Vito Ferro
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2022-dhq8q
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2022-dhq8q
1-Azasugar analogues of L-iduronic acid (L-IdoA) and D-glucuronic acid (D-GlcA) and their corresponding enantiomers were synthesized as potential pharmacological chaperones for mucopolysaccharidosis I (MPS I), a lysosomal storage disease caused by mutations in the gene encoding a-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 b-glucuronidase (b-GLU). The D-GlcA-configured 9 was a potent inhibitor of b-GLU and a moderate inhibitor of the endo-b-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.
Related Topics
Concepts
Heparanase
Chemistry
Glucuronic acid
Iduronic acid
Glucuronidase
Uronic acid
Biochemistry
Stereochemistry
Enantiomer
Glucuronidation
Glycosaminoglycan
Enzyme
Heparan sulfate
Microsome
Polysaccharide
Metadata
- Type
- preprint
- Language
- en
- Landing Page
- https://doi.org/10.26434/chemrxiv-2022-dhq8q
- https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/63534daa31107214caea86fd/original/synthesis-of-uronic-acid-1-azasugars-as-putative-inhibitors-of-a-iduronidase-b-glucuronidase-and-heparanase.pdf
- OA Status
- gold
- References
- 2
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4307256770
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
-
https://openalex.org/W4307256770Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.26434/chemrxiv-2022-dhq8qDigital Object Identifier
- Title
-
Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of a-Iduronidase, b-Glucuronidase and HeparanaseWork title
- Type
-
preprintOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2022Year of publication
- Publication date
-
2022-10-25Full publication date if available
- Authors
-
Gareth G. Doherty, Geraldine Jia Ming Ler, Norbert Wimmer, Paul V. Bernhardt, Roger A. Ashmus, David J. Vocadlo, Zachary Armstrong, G.J. Davies, Marco Maccarana, Jin‐Ping Li, Yasmin Kayal, Vito FerroList of authors in order
- Landing page
-
https://doi.org/10.26434/chemrxiv-2022-dhq8qPublisher landing page
- PDF URL
-
https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/63534daa31107214caea86fd/original/synthesis-of-uronic-acid-1-azasugars-as-putative-inhibitors-of-a-iduronidase-b-glucuronidase-and-heparanase.pdfDirect link to full text PDF
- Open access
-
YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
- OA URL
-
https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/63534daa31107214caea86fd/original/synthesis-of-uronic-acid-1-azasugars-as-putative-inhibitors-of-a-iduronidase-b-glucuronidase-and-heparanase.pdfDirect OA link when available
- Concepts
-
Heparanase, Chemistry, Glucuronic acid, Iduronic acid, Glucuronidase, Uronic acid, Biochemistry, Stereochemistry, Enantiomer, Glucuronidation, Glycosaminoglycan, Enzyme, Heparan sulfate, Microsome, PolysaccharideTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
0Total citation count in OpenAlex
- References (count)
-
2Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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