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Characterization of the recognition of blood group B trisaccharide derivatives by the lectin from Marasmius oreades using frontal affinity chromatography-mass spectrometry

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Abstract

A novel lectin from the mushroom Marasmius oreades (MOA) has been shown to bind to human blood group B oligosaccharides [1]. In the present work we examine the binding of a series of analogues of the blood group B-trisaccharide, αGal(1-3)[αFuc(1-2)]βGal-OR (1, R = (CH2)8COOMe). MOA was biotinylated and immobilized on a micro column (9.8 μL) for evaluation by Frontal Affinity Chromatography-Mass Spectrometry (FAC-MS) [2]. The trisaccharide 1 was found to be the epitope needed for maximum recognition (K d = 3.6 μM). A series of synthetic deoxygenated and O-methylated analogues of the B-trisaccharide (R = OMe) were then screened against the lectin, and the key structural elements for binding were determined. OH-4 of the β-Gal residue and OH-2 of the α-Gal residue were found to be critical for recognition. The FAC-MS technique also proved powerful in evaluating mixtures of compounds. Since the solution NMR structure and crystal structure of the B-trisaccharide are known [3], we propose the specific surface of the trisaccharide that is recognized by the lectin. Published in 2003.

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Authors and Affiliations

  1. Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2

    Brian P. Rempel & Ole Hindsgaul

  2. Department of Biological Chemistry, University of Michigan Medical School, Ann Arbor, MI, 48109-0606, USA

    Harry C. Winter & Irwin J. Goldstein

Authors
  1. Brian P. Rempel
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  2. Harry C. Winter
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  3. Irwin J. Goldstein
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  4. Ole Hindsgaul
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Rempel, B.P., Winter, H.C., Goldstein, I.J. et al. Characterization of the recognition of blood group B trisaccharide derivatives by the lectin from Marasmius oreades using frontal affinity chromatography-mass spectrometry. Glycoconj J 19, 175–180 (2002). https://doi.org/10.1023/A:1024297623445

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