81243-74-5Relevant 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.
SYNTHESIS OF AN OCTASACCHARIDE FRAGMENT OF THE POLYLACTOSAMINE SERIES BY A BLOCKWISE APPROACH
Alais, Jocelyne,Veyrieres, Alain
, p. 3345 - 3348 (2007/10/02)
Block synthesis of an octasaccharide, β-(1-3) linked tetramer of N-acetyllactosamine, is reported.Intermediate di- and tetrasaccharides were converted either into trichloroacetimidates acting as glycosyl donors or into vicinal diols acting as glycosyl acc