In search of specific and highly selective sugar clusters for cell receptors, such as membrane lectins, various disaccharides were coupled to small peptide cores through an amide bond. In a first step, the reducing disaccharides, i.e. lactose and three different dimannoses, were converted into glycosyl-pyroglutamyl-β-alanine derivatives. The free carboxylic group of these conjugates was then coupled to the α and ∊ amino groups of the core peptide (Lysn-Ala-Cys-NH2) with n = 1 to 5, with complete substitution leading to homogeneous glycoclusters. The thiol group of the cysteine residue was used to tag the glycosylated oligolysines upon reaction with fluorescein iodoacetamide. The affinity of these glycoclusters towards two plant lectins was assessed by surface plasmon resonance. The selectivity of their cell uptake was investigated by flow cytometry using two types of cells: a human hepatoma cell line (HepG2 cells) expressing the plasma membrane galactose-specific lectin, and monocyte-derived dendritic cells expressing the plasma membrane mannose-specific lectin. The glycoclusters containing four or five disaccharides were shown to bind plant lectins and cell surface membrane lectins with a narrow selectivity and with a high affinity.
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November 2002
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Research Article|
November 15 2002
Oligolysine-based saccharide clusters: synthesis and specificity
Natacha FRISON;
Natacha FRISON
1
Glycobiologie, Vectorologie et Trafic intracellulaire, Centre de Biophysique Moléculaire, CNRS, 1, rue Charles Sadron, F-45071 Orléans Cedex 2, France
1To whom correspondence should be addressed (e-mail frison@cnrs-orleans.fr).
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Philippe MARCEAU;
Philippe MARCEAU
Glycobiologie, Vectorologie et Trafic intracellulaire, Centre de Biophysique Moléculaire, CNRS, 1, rue Charles Sadron, F-45071 Orléans Cedex 2, France
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Annie-Claude ROCHE;
Annie-Claude ROCHE
Glycobiologie, Vectorologie et Trafic intracellulaire, Centre de Biophysique Moléculaire, CNRS, 1, rue Charles Sadron, F-45071 Orléans Cedex 2, France
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Michel MONSIGNY;
Michel MONSIGNY
Glycobiologie, Vectorologie et Trafic intracellulaire, Centre de Biophysique Moléculaire, CNRS, 1, rue Charles Sadron, F-45071 Orléans Cedex 2, France
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Roger MAYER
Roger MAYER
Glycobiologie, Vectorologie et Trafic intracellulaire, Centre de Biophysique Moléculaire, CNRS, 1, rue Charles Sadron, F-45071 Orléans Cedex 2, France
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Publisher: Portland Press Ltd
Received:
April 26 2002
Revision Received:
July 09 2002
Accepted:
July 15 2002
Accepted Manuscript online:
July 15 2002
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London ©2002
2002
Biochem J (2002) 368 (1): 111–119.
Article history
Received:
April 26 2002
Revision Received:
July 09 2002
Accepted:
July 15 2002
Accepted Manuscript online:
July 15 2002
Citation
Natacha FRISON, Philippe MARCEAU, Annie-Claude ROCHE, Michel MONSIGNY, Roger MAYER; Oligolysine-based saccharide clusters: synthesis and specificity. Biochem J 15 November 2002; 368 (1): 111–119. doi: https://doi.org/10.1042/bj20020673
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