Synthesis of Pro-Xylane: a new biologically active C-glycoside in aqueous media

  • Bioorg Med Chem Lett. 2009 Feb 1;19(3):845-9. doi: 10.1016/j.bmcl.2008.12.037.
Alexandre Cavezza  1 ,  Christophe Boulle ,  Amélie Guéguiniat ,  Patrick Pichaud ,  Simon Trouille ,  Louis Ricard ,  Maria Dalko-Csiba
Affiliations
  • 1. L'Oréal Recherche, Personal Care Chemistry, 93601 Aulnay sous Bois, Cedex, France.
PMID: 19135365 DOI: 10.1016/j.bmcl.2008.12.037
Abstract

The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane) was identified as the best activator of GAGs biosynthesis. Pro-Xylane was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic.

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