Norbert Wimmer
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View article: Purple Light-Promoted Ferrier Photobromination of O-Benzoylated Carbohydrates in Benzotrifluoride
Purple Light-Promoted Ferrier Photobromination of O-Benzoylated Carbohydrates in Benzotrifluoride Open
Our laboratory has previously reported on a contemporary Ferrier photobromination which circumvents critical limitations of the original reaction. The new conditions provide highly efficient and scalable routes to O-acetylated 5-C-bromosug…
View article: Efficient Synthesis of Fluorogenic Substrates for Mucopolysaccharidosis (MPS) IIIA and IIIB Via Aromatic α-Glycosylation with Thioglycosyl Donors
Efficient Synthesis of Fluorogenic Substrates for Mucopolysaccharidosis (MPS) IIIA and IIIB Via Aromatic α-Glycosylation with Thioglycosyl Donors Open
Sanfilippo syndrome (Mucopolysaccharidosis type III, or MPS III) is an inherited neurodegenerative disorder resulting from mutations in genes encoding lysosomal enzymes that sequentially degrade heparan sulfate. Currently, there are no app…
View article: Substrate reduction using a glucosamine analogue in Drosophila melanogaster and mouse models of Sanfilippo syndrome
Substrate reduction using a glucosamine analogue in Drosophila melanogaster and mouse models of Sanfilippo syndrome Open
Mucopolysaccharidosis (MPS) types III A and C are inherited neurodegenerative disorders resulting from the lack of a specific enzyme involved in heparan sulfate (HS) catabolism, leading to the accumulation of partially-degraded HS fragment…
View article: Synthesis of a deuterated disaccharide internal standard for LC-MS/MS quantitation of heparan sulfate in biological samples
Synthesis of a deuterated disaccharide internal standard for LC-MS/MS quantitation of heparan sulfate in biological samples Open
High levels of heparan sulfate (HS) are a marker for several mucopolysaccharidosis (MPS) disorders which are lysosomal storage diseases caused by genetic defects in HS-degrading enzymes. Quantitation of HS in biological samples is therefor…
View article: Amphiphilic Heparinoids as Potent Antiviral Agents against SARS-CoV-2
Amphiphilic Heparinoids as Potent Antiviral Agents against SARS-CoV-2 Open
Herein, we report the synthesis and biological evaluation of a novel series of heparinoid amphiphiles as inhibitors of heparanase and SARS-CoV-2. By employing a tailor-made synthetic strategy, a library of highly sulfated homo-oligosacchar…
View article: Site-Selective Photobromination of O-Acetylated Carbohydrates in Benzotrifluoride
Site-Selective Photobromination of O-Acetylated Carbohydrates in Benzotrifluoride Open
The Ferrier photobromination enables direct synthetic access to valuable 5-C-bromosugars but has limitations which restrict its broader use. The reaction is typically conducted in CCl4 heated at reflux with irradiation by broad spectrum, e…
View article: Synthetic Access to L-Guluronic Acid via Fluorine-Directed C-5 Epimerization
Synthetic Access to L-Guluronic Acid via Fluorine-Directed C-5 Epimerization Open
L-Guluronic acid is integral to the structures of alginates and to the pathogenesis of Pseudomonas aeruginosa. The exploitation of this hexose in both existing and new contexts is, however, limited by its prohibitively high commercial cost…
View article: Synthesis of a Deuterated Disaccharide Internal Standard for Lc-Ms/Ms Quantitation of Heparan Sulfate in Biological Samples
Synthesis of a Deuterated Disaccharide Internal Standard for Lc-Ms/Ms Quantitation of Heparan Sulfate in Biological Samples Open
View article: CCDC 2195774: Experimental Crystal Structure Determination
CCDC 2195774: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2195776: Experimental Crystal Structure Determination
CCDC 2195776: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2195773: Experimental Crystal Structure Determination
CCDC 2195773: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2195775: Experimental Crystal Structure Determination
CCDC 2195775: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Substrate reduction therapy in a<i>Drosophila melanogaster</i>model of Sanfilippo syndrome
Substrate reduction therapy in a<i>Drosophila melanogaster</i>model of Sanfilippo syndrome Open
Sanfilippo syndrome, or mucopolysaccharidosis (MPS) types A, B, C or D, are neurodegenerative lysosomal storage disorders resulting from the lack of a specific enzyme involved in heparan sulfate (HS) catabolism. Several treatments are unde…
View article: Synthesis of a Gal-ß-(1?4)-Gal disaccharide as a ligand for the fimbrial adhesin UcaD
Synthesis of a Gal-ß-(1?4)-Gal disaccharide as a ligand for the fimbrial adhesin UcaD Open
The disaccharide Gal-ß-(1?4)-Gal was recently identified as a ligand for the adhesin UcaD, a fimbrial protein used by Proteus mirabilis to adhere to exfoliated uroepithelial cells and colonise the urinary tract. To facilitate further studi…
View article: Synthesis of Uronic Acid 1‐Azasugars as Putative Inhibitors of α‐Iduronidase, β‐Glucuronidase and Heparanase**
Synthesis of Uronic Acid 1‐Azasugars as Putative Inhibitors of α‐Iduronidase, β‐Glucuronidase and Heparanase** Open
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 storag…
View article: Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of a-Iduronidase, b-Glucuronidase and Heparanase
Synthesis of Uronic Acid 1-Azasugars as Putative Inhibitors of a-Iduronidase, b-Glucuronidase and Heparanase Open
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 c…
View article: A Fluorogenic Heparan Sulfate Disaccharide for the Measurement of Heparanase Activity
A Fluorogenic Heparan Sulfate Disaccharide for the Measurement of Heparanase Activity Open
The endo-β-glucuronidase heparanase mediates mammalian heparan sulfate catabolism, and is of considerable medical interest due to its prominent role in cancer aggression and metastasis. Biochemical studies of heparanase are currently hampe…
View article: A Fluorogenic Heparan Sulfate Disaccharide for the Measurement of Heparanase Activity
A Fluorogenic Heparan Sulfate Disaccharide for the Measurement of Heparanase Activity Open
The endo-β-glucuronidase heparanase mediates mammalian heparan sulfate catabolism, and is of considerable medical interest due to its prominent role in cancer aggression and metastasis. Biochemical studies of heparanase are currently hampe…