Title of article
The first chemical synthesis of novel MeO-3-GlcUA derivative of hyaluronan-based disaccharide to elucidate the catalytic mechanism of hyaluronic acid synthases (HASs)
Author/Authors
Wei، نويسنده , , Guohua and Kumar، نويسنده , , Vipin and Xue، نويسنده , , Jun and Locke، نويسنده , , Robert D. and Matta، نويسنده , , Khushi L. Matta، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
3
From page
6543
To page
6545
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.
Keywords
MeO-3-GlcUA , Hyaluronic acid synthases (HASs) , phosphorylation , oligosaccharides
Journal title
Tetrahedron Letters
Serial Year
2009
Journal title
Tetrahedron Letters
Record number
1866677
Link To Document