The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) |
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| Authors: | Guohua Wei Vipin Kumar Robert D. Locke |
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| Affiliation: | a Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA
b State Key laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China |
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| Abstract: | The first chemical synthesis of MeO-3-GlcUAβ(1→3)GlcNAc-UDP to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs) is described. Construction of the desired β(1→3)-linked disaccharide 10 was achieved very efficiently by coupling MeO-3-GlcUA donor 3 with the suitable protected GlcNTroc acceptor 4 using BF3·Et2O as Lewis acid. Chemoselective removal of anomeric NAP, phosphorylation, hydrogenation, coupling with UMP-morpholidate, and finally complete deprotection gave the target compound 1 in good yield. |
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| Keywords: | MeO-3-GlcUA Hyaluronic acid synthases (HASs) Oligosaccharides Phosphorylation |
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