Synthesis of aromatic C-xylosides by position inversion of glucose.
Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position 1 becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming.
Malmberg
Jesper
J
Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
Mani
Katrin
K
Säwén
Elin
E
Wirén
Anders
A
Ellervik
Ulf
U
D016475:3T3 Cells; D000818:Animals; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005947:Glucose / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008969:Molecular Sequence Data
D006027:Glycosides; D007202:Indicators and Reagents; C010807:xylosides; D005947:Glucose