Synthesis of aromatic C-xylosides by position inversion of glucose

Jesper Malmberg; Katrin Mani; Elin Säwén; Anders Wirén; Ulf Ellervik

doi:10.1016/j.bmc.2006.05.068

Synthesis of aromatic C-xylosides by position inversion of glucose

Bioorg Med Chem. 2006 Oct 1;14(19):6659-65. doi: 10.1016/j.bmc.2006.05.068. Epub 2006 Jun 16.

Authors

Jesper Malmberg¹, Katrin Mani, Elin Säwén, Anders Wirén, Ulf Ellervik

Affiliation

¹ Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.

PMID: 16782347
DOI: 10.1016/j.bmc.2006.05.068

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

3T3 Cells
Animals
Carbohydrate Sequence
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Glucose / chemistry*
Glycosides / chemical synthesis*
Glycosides / chemistry*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mice
Molecular Sequence Data

Substances

Glycosides
Indicators and Reagents
xylosides
Glucose