In the present work, the synthesis of a hexasaccharide partial sequence of hyaluronan equipped with a terminal azido moiety is reported. This hexasaccharide can be used for the attachment on surfaces by means of click chemistry and after suitable deprotection for biophysical studies.
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http://dx.doi.org/10.3762/bjoc.11.67 | DOI Listing |
Angew Chem Int Ed Engl
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
Globo H, a specific carbohydrate antigen overexpressed on various human malignancies, has attracted considerable interest as an antigenic target for anticancer vaccine development. Despite several Globo H-based carbohydrate vaccines that have been designed, efficient access to Globo H hexasaccharide antigen and development of powerful adjuvants for enhancing antitumor immunity remain challenging. Herein, we reported a streamlined chemoenzymatic approach to prepare this hexasaccharide antigen, relying on chemical synthesis of Gb5 pentasaccharide by a stereoconvergent [2+3] strategy and subsequent enzymatic α-fucosylation to easily install α1,2-fucose residue.
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November 2024
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
This study focuses on the synthesis of a series of oligo--(1→6)-D-galactopyranosides bearing -D-galactofuranosyl residues at O-2 and/or O-3, which relate structurally to fragments of glucuronoxylomannogalactan (GXMGal) from the fungal pathogen that causes severe diseases in immunocompromised patients. The preparation of target compounds is based on the use of a selectively O-protected N-phenyltrifluoroacetimidoyl galactopyranoside donor with an allyl group at O-2, levulinoyl group (Lev) at O-3, pentafluorobenzoyl (PFB) group at O-4, and fluorenylmethoxycarbonyl (Fmoc) group at O-6. The choice of protecting groups for this donor ensures the stereospecific formation of (1→6)-glycosidic bonds due to the stereodirecting effect of acyls at O-3, O-4, and O-6.
View Article and Find Full Text PDFCarbohydr Res
January 2025
Graduate School of Sustainability Science, Department of Agricultural Science, Tottori University, Tottori, 680-8553, Japan; Department of Agricultural, life and Environmental Sciences, Faculty of Agriculture, Tottori University, Tottori, 680-8553, Japan; The United Graduate School of Agricultural Sciences, Tottori University, Tottori, 680-8553, Japan. Electronic address:
Muscle tissue is stabilized by the strong interaction between laminin and matriglycan. Matriglycan is a polysaccharide composed of the repeating disaccharide, -3Xylα1-3GlcAβ1-, and is a pivotal part of the core M3 O-mannosyl glycan. Patients with muscular dystrophy cannot synthesize matriglycan or the core M3 O-mannosyl glycan due to a defect in or the lack of glycosyltransferases owing to glycan synthesis.
View Article and Find Full Text PDFAnal Chem
November 2024
The Rosalind Franklin Institute, Harwell Campus, Didcot OX11 0FA, U.K.
Commun Chem
September 2024
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India.
Zwitterionic polysaccharides (ZPSs) present on the surface of a common gut commensal Bacteroides fragilis are endowed with unique immunological properties as they can directly bind to T-cells in the absence of protein conjugation. ZPSs are therefore considered to be potential antigens for the development of totally carbohydrate-based vaccines. Herein, we disclose the first total synthesis of a highly branched phosphorylated zwitterionic capsular polysaccharide repeating unit of Bacteroides fragilis.
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