227601-52-7Relevant academic research and scientific papers
Synthesis of oligosaccharides related to HNK-1 antigen. 2. synthesis of β-propyl 3?-O-(3-o-sulfo-β-d-glucuronopyranosyl)-lacto-n-tetraoside
Kononov,Kornilov,Sherman,Zyryanov,Zatonsky,Shashkov,Nifant'ev
, p. 537 - 550 (2007/10/03)
A derivative of allyl 3Prime;-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-lactoside with a free OH group at C-4GlcNAc was glycosylated with trichloroacetimidate of selectively protected GlcA(β1→3)Galα disaccharide in dichloromethane in the presence of trimethylsilyl inflate, resulting in a pentasaccharide product with an 82% yield. This product was converted to monohydroxy derivative with a free OH group at C-3GlcA via the formation and the subsequent opening of the 6,3-lactone ring in the glucuronic acid residue. The 3-O-sulfation of the monohydroxy derivative, the removal of the protective groups, and the reduction of the allyl aglycon yielded the pentasaccharide propyl glycoside NaSO 3-3GlcA(β1→3)Gal(β1→4)GlcNAc(β1→3) Gal(β1→4)Glcβ-OPr, comprising the oligosaccharide chain of the SGGL-1 glycolipid, which is recognized by HNK-1 antibodies. NaSO3-3GlcA(β1→3)GalβOAll, GlcA(β1→3)Gal(β1→4)GlcNAc(β1→3)Gal(β1→4) GlcβOPr, and GlcA(β1→3)GalβOAll were synthesized in a similar way.
