首次化学合成基于透明质酸的二糖新型甲氧基-3-葡萄糖醛酸衍生物，以阐明透明质酸合酶（HASs）的催化机制。
The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs).
作者信息
Wei Guohua, Kumar Vipin, Xue Jun, Locke Robert D, Matta Khushi L
机构信息
Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
出版信息
Tetrahedron Lett. 2009 Nov 25;50(47):6543-6545. doi: 10.1016/j.tetlet.2009.09.042.
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 BF(3(.) )Et(2)O 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.
摘要
描述了首次化学合成MeO-3-GlcUAβ(1→3)GlcNAc-UDP以阐明透明质酸合酶（HASs）的催化机制。通过使用BF(3(.) )Et(2)O作为路易斯酸，将MeO-3-GlcUA供体3与合适的受保护的GlcNTroc受体4偶联，非常高效地构建了所需的β(1→3)连接的二糖10。化学选择性去除异头NAP、磷酸化、氢化、与UMP-吗啉代化物偶联，最后完全脱保护，以良好的产率得到目标化合物1。
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