Synthesis of the matriglycan hexasaccharide, -3Xylα1-3GlcAβ1-trimer and its interaction with laminin. Issue 43 (21st October 2022)

• Record Type: Journal Article
• Authors: Tamura, Takahiro; Omura, Yuka; Kotera, Kota; Ito, Ryota; Ohno, Shiho; Manabe, Noriyoshi; Yamaguchi, Yoshiki; Tamura, Jun-ichi
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 43(2022)
• Page Start: 8489
• Page End: 8500
• Publication Date: 2022-10-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01388f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Matriglycan hexasaccharide (-3Xylα1-3GlcAβ1)3 -O(C2 H4 O)3 CH2 CCH and the biotin conjugate was synthesized. The hexasaccharide showed good interaction with laminin-G-like domains 4 and 5 of laminin-α2 using saturation transfer difference-NMR and bio-layer interferometry. Abstract : Matriglycan, a polysaccharide that is a pivotal part of the core M3 O -mannosyl glycan composed of the repeating disaccharide -3Xylα1-3GlcAβ1-, interacts with laminin to stabilize muscle tissue. We herein report the synthesis of matriglycan-repeating hexasaccharides equipped with an alkyne linker to form glycoconjugates. The key step in the formation of an α-linked xylosyl glycoside was resolved by solvent-specific separation from an anomeric mixture. Successful glycan elongation was regio- and stereoselectively performed to obtain (-3Xylα1-3GlcAβ1)3 -O(C2 H4 O)3 CH2 CCH and the biotin conjugate. We also investigated interactions between matriglycan hexasaccharides and laminin-G-like domains 4 and 5 of laminin-α2 using saturation transfer difference-NMR. The dissociation constant obtained from bio-layer interferometry was estimated to be 7.5 × 10 −8 M. These results indicate that a chemical approach may be applied to the reconstruction of muscle tissue.