Anti-Lea monoclonal antibody SPM 522 recognizes an extended Lea epitope

Jegatheeswaran, Sinthuja; Guillemineau, Mickael; Giovane, Richard; Borrillo, Louis; Liao, Liang; Kuir, Deng; Auzanneau, France‐Isabelle

doi:10.1016/j.bmc.2022.116628

Cited by 2 publications

(4 citation statements)

References 48 publications

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“…The fact that this minor component cannot be separated from tetrasaccharide 4 using gel exclusion or silica gel chromatography indicates that it is similar in size and polarity to the tetrasaccharide. These results suggest that the aminononyl glycoside GlcNAc-(1,3)-Le a tetrasaccharide 4 also adopts a minor conformation in solution as we have reported for the aminohexyl glycoside of Le a …”

Section: Resultssupporting

confidence: 80%

“…These signals correspond, respectively, to H-1, H-5, and H-6 of an α-fucosyl residue. While the signal overlap does not allow further characterization of this minor (∼10%) component, the observed shifts for this fucosyl residue match the chemical shifts that we have reported for a minor conformation that we observed for the aminohexyl glycoside of the Le a trisaccharide . The fact that this minor component cannot be separated from tetrasaccharide 4 using gel exclusion or silica gel chromatography indicates that it is similar in size and polarity to the tetrasaccharide.…”

Section: Resultssupporting

confidence: 47%

“…Although the compound is homogeneous by TLC, a minor set of signals at 4.96, 4.36, and 1.20 ppm that do not belong to tetrasaccharides 4 or 5 can also be seen in 1 characterization of this minor (∼10%) component, the observed shifts for this fucosyl residue match the chemical shifts that we have reported for a minor conformation that we observed for the aminohexyl glycoside of the Le a trisaccharide. 39 The fact that this minor component cannot be separated from tetrasaccharide 4 using gel exclusion or silica gel chromatography indicates that it is similar in size and polarity to the tetrasaccharide. These results suggest that the aminononyl glycoside GlcNAc-(1,3)-Le a tetrasaccharide 4 also adopts a minor conformation in solution as we have reported for the aminohexyl glycoside of Le a .…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…These results suggest that the aminononyl glycoside GlcNAc-(1,3)-Le a tetrasaccharide 4 also adopts a minor conformation in solution as we have reported for the aminohexyl glycoside of Le a . 39 To obtain final compounds 6, 8, and 10, the 9-chlorononyl glycosides 43, 45, and 51 were treated with sodium azide in DMF at 80 °C, and the resulting 9-azidononyl intermediates 55−57 were purified by chromatography before deprotection (Scheme 7). Importantly, the full conversion of chlorononyl glycosides 43, 45, and 51 to azidononyl glycosides 55, 56, and 57, respectively, was confirmed unquestionably by the complete disappearance in the 1 H NMR spectra of triplets (2H, J = 6.7 or 6.8 Hz) at 3.50 or 3.51 ppm that correlate to methylene carbon signals at 45.1 or 45.2 ppm in the HSQC and account for CH 2 Cl in the tetra-or pentasaccharides 43, 45, and 51.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Synthesis of Dimeric Lewis A and Lewis B–Lewis A Tumor-Associated Carbohydrate Antigen Oligosaccharide Fragments

2023

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Despite the interesting potential of tumor-associated carbohydrate antigens (TACAs) dimLe a and Le b Le a to develop anticancer immunotherapies, little research has been conducted on these antigens. In our quest to discover fragments of these TACAs that could be targeted for the development of anticancer therapeutics, we report the synthesis of eight tri-to pentasaccharide fragments of these oligosaccharides. Unforeseen synthetic challenges are reported such as the incompatibility of a bromoalkyl glycoside in the reduction conditions needed to reduce a trichloroacetamide, the mismatched reactivities in a 2 + 1 synthetic strategy, and the surprising greater reactivity of a C-4 GlcNAc hydroxyl group versus that of the galactosyl OH-3 in the selective glycosylation of a trisaccharide diol. The desired final compounds were eventually obtained following a stepwise approach as nonyl or 9-aminononyl glycosides after one-step deprotection reactions in dissolving metal conditions. The 9-aminononyl glycosides will be conjugated to carrier proteins and the nonyl pentasaccharide glycoside will be used as a soluble inhibitor in binding experiments. In contrast, the nonyl tetrasaccharide glycosides are poorly soluble in water and their use in biochemical experiments will be limited.

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Section: Resultssupporting

confidence: 80%

Section: Resultssupporting

confidence: 47%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Synthesis of Dimeric Lewis A and Lewis B–Lewis A Tumor-Associated Carbohydrate Antigen Oligosaccharide Fragments

2023

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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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Anti-Lea monoclonal antibody SPM 522 recognizes an extended Lea epitope

Cited by 2 publications

References 48 publications

Synthesis of Dimeric Lewis A and Lewis B–Lewis A Tumor-Associated Carbohydrate Antigen Oligosaccharide Fragments

Synthesis of Dimeric Lewis A and Lewis B–Lewis A Tumor-Associated Carbohydrate Antigen Oligosaccharide Fragments

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

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