Synthesis of a Lewis b hexasaccharide thioglycoside donor and its use towards an extended mucin core Tn heptasaccharide structure and a photoreactive biotinylated serine linked hexasaccharide

Hollinger, Martin; Bonaccorsi, Filippo; Cheallaigh, Aisling Ní; Oscarson, Stefan

doi:10.1039/d2ob00477a

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00477a

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Synthesis of a Lewis b hexasaccharide thioglycoside donor and its use towards an extended mucin core Tn heptasaccharide structure and a photoreactive biotinylated serine linked hexasaccharide

Martin Hollinger

Filippo Bonaccorsi

Aisling Ní Cheallaigh

et al.

Abstract: Investigation into Heliobacter pylori binding to Lewis b (Leb) antigens through the blood group antigen binding adhesion protein (BabA) requires structurally well-defined tools. A Leb hexasaccharide thioglycoside donor was chemically...

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2024

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Cited by 2 publications

References 39 publications

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Harvey

2024

Mass Spectrometry Reviews

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The use of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of carbohydrates and glycoconjugates is a well‐established technique and this review is the 12th update of the original article published in 1999 and brings coverage of the literature to the end of 2022. As with previous review, this review also includes a few papers that describe methods appropriate to analysis by MALDI, such as sample preparation, even though the ionization method is not MALDI. The review follows the same format as previous reviews. It is divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of computer software for structural identification. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other general areas such as medicine, industrial processes, natural products and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. MALDI is still an ideal technique for carbohydrate analysis, particularly in its ability to produce single ions from each analyte and advancements in the technique and range of applications show little sign of diminishing.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Harvey

2024

Mass Spectrometry Reviews

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Synthesis of the H-type 1 and Lewis B antigens as 6-aminohexyl glycosides

Pickles,

Auzanneau

2024

Can. J. Chem.

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The LebLea heptasaccharide is a TACA that was isolated from the human colonic adenocarcinoma cell line Colo205 and is a good target for the development of anti-cancer immunotherapeutics. However, it displays on its reducing end the Leb tetrasaccharide: α-L-Fucp-(1→2)-β-D-Galp-(1→3)-[α-L-Fucp-(1→4)]-D-GlcNAcp and the H-type 1 (H-1 antigen) trisaccharide: α-L-Fucp-(1→2)-β-D-Galp-(1→3)-D-GlcNAcp that are also found on non cancerous tissues. To discover analogues or fragments of LebLea that could be used as immunotherapeutics while not triggering immune responses against Leb and the H-1 antigen, we have synthesised the Leb tetrasaccharide hexyl glycoside and the Leb and H-1 antigens aminohexyl glycosides to be used in ELISA experiments. We describe an improved preparation of the 6-O-benzyl-2,3,4-tri-O-acetyl-α-D-galactopyranosyl bromide in neutral conditions and demonstrate the importance of appropriately “matching” the reactivity of acceptors with that of glycosyl donors. Mono- and di-fucosylation of a disaccharide diol acceptor with per-benzylated thioethyl fucoside activated in situ with bromine and under halide ion catalysis is described and our results are compared to literature reports. We observed that our fucosylation reactions required higher equivalents of fucosyl donor and extended reaction times than previously reported. We propose that the protecting groups on the galactosyl unit led to a reduced reactivity of the acceptor. The protected intermediates were converted to 6-azido hexyl glycosides and submitted to dissolving metal conditions to give 6-aminohexyl glycosides. We also prepared the n-hexyl trisaccharide glycoside Leb that will be used as a soluble antigen in competitive ELISA experiments.

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Synthesis of a Lewis b hexasaccharide thioglycoside donor and its use towards an extended mucin core Tn heptasaccharide structure and a photoreactive biotinylated serine linked hexasaccharide

Abstract: Investigation into Heliobacter pylori binding to Lewis b (Leb) antigens through the blood group antigen binding adhesion protein (BabA) requires structurally well-defined tools. A Leb hexasaccharide thioglycoside donor was chemically...

Cited by 2 publications

References 39 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Synthesis of the H-type 1 and Lewis B antigens as 6-aminohexyl glycosides

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