The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

Matsuo, Ichiro; Isomura, Megumi; Ajisaka, Katsumi

doi:10.1016/s0040-4039(99)00930-2

Cited by 20 publications

(14 citation statements)

References 15 publications

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“…Unfortunately, the collective synthesis of these complex glycans, especially the asymmetrical Core M2 structures is very challenging. Previous chemical or chemoenzymatic synthesis mainly focused on the simple Core M1 glycans with branching structures I – III 5 , and the phosphorylated Core M3 trisaccharide 6 . Except for a symmetrical Core M2 trisaccharide core structure 7 , all other Core M2 symmetrical and asymmetrical structures have not been synthesized.…”

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confidence: 99%

Chemoenzymatic Assembly of Mammalian O‐Mannose Glycans

et al. 2018

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O-Mannose glycans, a family of highly heterogeneous complex glycans account up to 30% of total O-glycans in brain. Previous synthesis and functional studies only focused on the Core M3 O-mannose glycans of α-dystroglycan which are a causative factor for various muscular diseases. In this study, a highly efficient chemoenzymatic strategy was developed that enabled the first collective synthesis of 63 Core M1 and Core M2 O-mannose glycans. This chemoenzymatic strategy features the gram-scale chemical synthesis of 5 judiciously designed core structures, and the diversity-oriented modification of the core structures with 3 enzyme modules to provide 58 complex O-mannose glycans in a linear sequence that does not exceed 4 steps. Of note, 55 of these O-mannose glycans are synthesized for the first time. Using the printed O-mannose glycan array, the human brain protein CD33, a key factor in the modulation of Alzheimer’s disease was identified as strongly binding to sialylated Core M1 and Core M2.

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confidence: 99%

Chemoenzymatic Assembly of Mammalian O‐Mannose Glycans

et al. 2018

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“…To date, only a few O‐mannosyl glycans have been prepared . A core M1 tetrasaccharide (Figure , M102 ) was first synthesized in 1999,, and later two lower homologues were obtained ( M100 , M101 ). Most recently, Cao and co‐workers prepared six core M1 structures ( M100 , M101 , M102 , M104 , M105 , and M102G ) by employing a chemoenzymatic approach .…”

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confidence: 99%

Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans

et al. 2018

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OMannosylation is av ital protein modification involved in brain and muscle development whereas the biological relevance of O-mannosyl glycans has remained largely unknown owing to the lacko fs tructurally defined glycoforms.A ne fficient scaffold synthesis/enzymatic extension (SSEE) strategy was developed to prepare such structures by combining gram-scale convergent chemical syntheses of three scaffolds and strictly controlled sequential enzymatic extension catalyzedb yg lycosyltransferases.I nt otal, 45 O-mannosyl glycans were obtained, covering the majority of identified mammalian structures.S ubsequent glycan microarraya nalysis revealed fine specificities of glycan-binding proteins and specific antisera.

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“…[7] A core M1 tetrasaccharide (Figure 2, M102 ) was first synthesized in 1999, [7c,d] and later two lower homologues were obtained ( M100 , M101 ). Most recently, Cao and coworkers prepared six core M1 structures ( M100 , M101 , M102 , M104 , M105 , and M102G ) by employing a chemoenzymatic approach.…”

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confidence: 99%

“…Most recently, Cao and coworkers prepared six core M1 structures ( M100 , M101 , M102 , M104 , M105 , and M102G ) by employing a chemoenzymatic approach. [7a] Glycopeptides harboring basic O-mannosyl structures (e.g., M101 , [8] M102 , [9] core M0, [7e] M000 , [10] or core M3 [11] ) have also been generated. Nevertheless, the majority of O-mannosyl glycans (especially core M2 branched structures) are still not accessible, which has hampered our in-depth understanding of O mannosylation.…”

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confidence: 99%

Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans

et al. 2018

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O Mannosylation is a vital protein modification involved in brain and muscle development whereas the biological relevance of O-mannosyl glycans has remained largely unknown owing to the lack of structurally defined glycoforms. An efficient scaffold synthesis/enzymatic extension (SSEE) strategy was developed to prepare such structures by combining gram-scale convergent chemical syntheses of three scaffolds and strictly controlled sequential enzymatic extension catalyzed by glycosyltransferases. In total, 45 O-mannosyl glycans were obtained, covering the majority of identified mammalian structures. Subsequent glycan micro-array analysis revealed fine specificities of glycan-binding proteins and specific antisera.

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The first synthesis of neu5Acα2-3Galβ1-4GlcNAcβ1-2Manα1-ser — a newly discovered component of α-dystroglycan

Cited by 20 publications

References 15 publications

Chemoenzymatic Assembly of Mammalian O‐Mannose Glycans

Chemoenzymatic Assembly of Mammalian O‐Mannose Glycans

Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans

Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans

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