176300-27-9Relevant academic research and scientific papers
Synthetic α,β-(1→4)-Glucan oligosaccharides as models for heparan sulfate. Part II
Wessel, Hans Peter,Minder, Rudolf,Englert, Gerhard
, p. 201 - 216 (2007/10/03)
α,β-(1→4)-Glucan oligosaccharides were prepared as models for heparan sulfate with the simplifying assumptions that carboxyl-reduction and sulfation of heparan sulfate does not decrease the SMC antiproliferative activity and that N-sulfates in glucosamines can be replaced by O-sulfates. The target saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (1) with hepta-O-acetyl-α-maltosyl bromide (2) furnished trisaccharide 3 which was deprotected to α-D-Glc-(1→4)-β-D-Glc-(1→4)-α-D-Glc(1→OCH 3) (5) or, alternatively, converted to the trisaccharide glycosyl acceptor (8) with one free hydroxyl function (4″-OH). Further silver triflate mediated glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the tetrasaccharide β-D-Glc-(1→4)-α-D-Glc-(1→4)-β-D-Glc-(1→4)- α-D-Glc-(1→OCH3) (11) and the pentasaccharide [α-D-Glc-(1→4)-β-D-Glc-(1→4)] 2-α-D-Glc-(1→KDCH3) (14). The trisaccharides 3, 4, 6, and 8 as well as pentasaccharide 12 were fully characterized by 1H, 3, 8 and 12 also by 13C NMR spectroscopy Assignments were possible using 1D TOCSY, in some cases supplemented by 2D T-ROESY, 1H,1H 2D COSY, and 1H-detected one-bond and multiple-bond 1H,13C 2D COSY experiments.
