Corrigendum: Characterization of <i>Meiothermus taiwanensis</i> Galactokinase and its Use in the One‐Pot Enzymatic Synthesis of Uridine Diphosphate‐Galactose and the Chemoenzymatic Synthesis of the Carbohydrate Antigen Stage Specific Embryonic Antigen‐3

Li, Si-Peng; Hsiao, Wei-Chen; Yu, Ching‐Ching; Chien, Wei-Ting Kary; Lin, Hong-Jyune; Huang, Li-De; Lin, Chien‐Hung; Wu, Wan-Chen; Wu, Shih‐Hsiung; Lin, Chun‐Cheng

doi:10.1002/adsc.202000563

Cited by 3 publications

(2 citation statements)

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“…24,25 Two main classes of enzymes are responsible for the in vivo synthesis of sugar-1-phosphates from non-activated monosaccharides: galactokinases (GalKs) which catalyse the ATP dependant phosphorylation of α-D-galactose (Gal) and N-acetylhexosamine kinases (NahKs, also known as HexNAcKs) which phosphorylate both N-acetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc). Many well characterised examples of GalKs have been reported, [26][27][28][29][30][31][32][33][34][35][36] while only a few NahKs have been previously investigated. 37,38 Both classes are highly promiscuous, exhibiting a broad tolerance to natural and derivatised monosaccharides.…”

Section: Introductionmentioning

confidence: 99%

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-fluorinated Monosaccharides

Keenan

Parmeggiani

Malassis

et al. 2020

Cell Chemical Biology

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Fluorinated sugar-1-phosphates are of emerging importance as intermediates in the chemical and biocatalytic synthesis of modified oligosaccharides, as well as probes for chemical biology.Here we present a systematic study of the activity of a wide range of anomeric sugar kinases (galacto-and N-acetylhexosamine kinases) against a panel of fluorinated monosaccharides, leading to the first examples of polyfluorinated substrates accepted by this class of enzymes. We have discovered four new N-acetylhexosamine kinases with a different substrate scope, thus expanding the number of homologs available in this subclass of kinases. Lastly, we have solved the crystal structure of a galactokinase in complex with 2-deoxy-2fluoro galactose, giving insight into changes in the active site that may account for the specificity of the enzyme towards certain substrate analogues.Scheme 1. Kinase-mediated synthesis of fluorosugar-1-phosphates and their applications.

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Section: Introductionmentioning

confidence: 99%

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-fluorinated Monosaccharides

Keenan

Parmeggiani

Malassis

et al. 2020

Cell Chemical Biology

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show abstract

“…Two main classes of enzymes are responsible for the in vivo synthesis of sugar-1-phosphates from non-activated monosaccharides: galactokinases (GalKs) which catalyse the ATP dependant phosphorylation of galactose (Gal) and N-acetylhexosamine kinases (NahKs, also known as HexNAcKs) which phosphorylate both Nacetylglucosamine (GlcNAc) and N-acetylgalactosamine (GalNAc). Many well characterised examples of GalKs have been reported, [29][30][31][32][33][34][35][36][37][38][39] while only a few NahKs have been previously investigated. 40,41 Both classes are highly promiscuous, exhibiting a broad tolerance to natural and derivatised monosaccharides.…”

Section: Introductionmentioning

confidence: 99%

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-Fluorinated Monosaccharides

Keenan

Parmeggiani

Malassis

et al. 2020

Preprint

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A Modular Chemoenzymatic Synthesis of Disialosyl Globopentaosylceramide (DSGb5Cer) Glycan

Adak

Kuo

et al. 2020

J. Org. Chem.

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The total synthesis of the oligosaccharide moiety of disialosyl globopentaosylceramide (DSGb5 Cer), a dominant ganglioside isolated from malignant renal cell carcinoma tissues, is reported. The synthetic strategy relies on a chemical α(2,6)-sialylation at the internal GalNAc unit of a Gb5 pentasaccharide backbone that furnishes a Neu5Acα(2,6)GalNAc-linked hexasaccharide, suitable for an enzymatic α(2,3)-sialylation of the terminal Gal residue to construct a heptasaccharide glycan. Convergent access to this key α(2,6)-sialylated hexasaccharide was also achieved through a [3+3] glycosylation building upon a Galβ(1,3)[Neu5Acα(2,6)]GalNAc-based trisaccharide donor and a Gb3 acceptor. The synthetic DSGb5 glycan bearing a 6-azidohexyl aglycon at the reducing end could undergo further regioselective functionalization. This approach represents a viable chemoenzymatic method for accessing complex ganglioside glycans and should be useful for the synthesis and biological investigation of DSGb5 derivatives.

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Corrigendum: Characterization of Meiothermus taiwanensis Galactokinase and its Use in the One‐Pot Enzymatic Synthesis of Uridine Diphosphate‐Galactose and the Chemoenzymatic Synthesis of the Carbohydrate Antigen Stage Specific Embryonic Antigen‐3

Cited by 3 publications

References 0 publications

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-fluorinated Monosaccharides

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-fluorinated Monosaccharides

Profiling Substrate Promiscuity of Wild-Type Sugar Kinases for Multi-Fluorinated Monosaccharides

A Modular Chemoenzymatic Synthesis of Disialosyl Globopentaosylceramide (DSGb5Cer) Glycan

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