53167-37-6Relevant articles and documents
Chemoenzymatic Synthesis of Sialyl Sulfo-Oligosaccharides as Potent Siglec-8 Ligands via Transglycosylation Catalyzed by Keratanase II
Yuge, Shiori,Tateishi, Ayaka,Numata, Keiji,Ohmae, Masashi
, p. 316 - 325 (2022/01/04)
Sialyl type-II sulfo-oligosaccharides are gaining much attention as bioactive ligands for Siglecs. In this study, we have achieved the first synthesis of sialyl type-II sulfo-oligosaccharides chemoenzymatically by utilizing the transglycosylation activity of keratanase II. The oxazoline derivative of α(2→3)-sialylated 6,6′-di-sulfo-LacNAc (3) was newly designed as the glycosyl donor for enzymatic transglycosylation. Keratanase II efficiently catalyzed the transglycosylation of 3 with two kinds of glycosyl acceptors, 6-sulfo-Lewis X and 6,6′-di-sulfo-LacNAc derivatives, providing sialyl sulfo-hexasaccharide (1) and sialyl sulfo-pentasaccharide (2) with 86 and 95% yields, respectively. The products 1 and 2 showed higher affinity to Siglec-8 with KD 70 and 25 μmol·L-1, respectively, compared to the known ligand of the α(2→3)-sialylated 6,6′-di-sulfo-Lewis X with KD 185 μmol·L-1. Thus, this study will advance not only the study of Siglec-8 biology but also the exploration of functions of sialyl sulfo-oligosaccharides having various microstructures.
A facile synthesis of benzyl 2-acetamido-6-O-acetyl-4-O-(6-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside, a key intermediate for the synthesis of O-α-L-fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranos
Rana, Surjit S.,Matta, Khushi L.
, p. C18 - C21 (2007/10/02)
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