Biotinylated Oligo-α-(1 → 4)-d-galactosamines and Their N-Acetylated Derivatives: α-Stereoselective Synthesis and Immunology Application

Biotinylated Oligo-α-(1 → 4)-d-galactosamines and Their N-Acetylated Derivatives: α-Stereoselective Synthesis and Immunology Application Full article

Journal

Journal of the American Chemical Society
ISSN: 0002-7863 , E-ISSN: 1520-5126

Output data

Year: 2020, Volume: 142, Number: 3, Pages: 1175-1179 Pages count : 5 DOI: 10.1021/jacs.9b11703

Authors

Kazakova Ekaterina D ¹ , Yashunsky Dmitry V ¹ , Krylov Vadim B ¹ , Bouchara Jean-Philippe ² , Cornet Murielle ³ , Valsecchi Isabel ⁴ , Fontaine Thierry ⁴ , Latgé Jean-Paul ^5,4 , Nifantiev Nikolay E ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation
2	Laboratoire de Parasitologie Mycologie, CHU Angers, 49933 Angers cedex 9, France
3	University of Grenoble Alpes, CNRS, CHU Grenoble Alpes, Grenoble INP, TIMC-IMAG, 38043 Grenoble, France
4	Unité des Aspergillus, Institut Pasteur, 75724 Paris, France
5	School of Medicine, University of Crete, Heraklion, Greece

Using 3-O-benzoyl-4,6-O-di-tert-butylsilylidene-2-azido-2-deoxy-selenogalactoside, biotinylated oligo-α-(1 → 4)-d-galactosamines comprising from two to six GalN units were prepared for the first time together with their N-acetylated derivatives. The combination of blocking groups used herein provided stereocontrol for the α-stereospecific glycosylation, to show also high efficiency of phenyl 2-azido-2-deoxy-selenogalactosides as glycosyl donors. The obtained glycoconjugates are related to fragments of exopolysaccharide galactosaminogalactan (GG) found in Aspergillus fumigatus, which is the most important airborne human fungal pathogen in industrialized countries. The synthesized glycoconjugates were arrayed on streptavidin-coated plates and used to investigate the GG epitopes recognized by mouse monoclonal antibodies against GG and by human antibodies in the sera of patients with aspergillosis. The obtained data showed that the oligo-α-(1 → 4)-d-galactosamines and their N-acetylated derivatives allowed the first precise analysis of the specificity of the antibody responses to this extremely complex fungal polysaccharide.

Kazakova E.D. , Yashunsky D.V. , Krylov V.B. , Bouchara J-P. , Cornet M. , Valsecchi I. , Fontaine T. , Latgé J-P. , Nifantiev N.E.
Biotinylated Oligo-α-(1 → 4)-d-galactosamines and Their N-Acetylated Derivatives: α-Stereoselective Synthesis and Immunology Application
Journal of the American Chemical Society. 2020. V.142. N3. P.1175-1179. DOI: 10.1021/jacs.9b11703 WOS Scopus OpenAlex

≡ Web of science:	WOS:000509425600009
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≡ OpenAlex:	W3000236050