1. Synthesis of Pro-Xylane: a new biologically active C-glycoside in aqueous media.
- Author
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Cavezza A, Boulle C, Guéguiniat A, Pichaud P, Trouille S, Ricard L, and Dalko-Csiba M
- Subjects
- Alcohols chemistry, Carbon chemistry, Drug Design, Humans, Ketones chemistry, Models, Chemical, Proteoglycans chemistry, Solvents chemistry, Temperature, Water chemistry, Xylose chemistry, Chemistry, Pharmaceutical methods, Glycosaminoglycans chemistry, Glycosides chemistry
- 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.
- Published
- 2009
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