Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2008-12-13 , DOI: 10.1016/j.bmcl.2008.12.037 Alexandre Cavezza , Christophe Boulle , Amélie Guéguiniat , Patrick Pichaud , Simon Trouille , Louis Ricard , Maria Dalko-Csiba
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-XylaneTM) was identified as the best activator of GAGs biosynthesis. Pro-XylaneTM 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.
中文翻译:
Pro-Xylane TM的合成:水性介质中的一种新型生物活性C-糖苷
Lubineau的反应的范围和限制为C-糖苷(化合物的合成进行了评价1 - 13)。还实现了侧链羰基的进一步转化(化合物16 – 23)。在木糖的情况下,对这两个步骤的优化进行了研究。已显示某些化合物可刺激硫酸化糖胺聚糖(GAG)的合成。化合物20(称为Pro-Xylane TM)被确定为GAGs生物合成的最佳活化剂。Pro-Xylane TM 该产品是在符合“绿色化学”原理的环保条件下开发的,并于2006年9月投放市场。该化合物是化妆品中使用的“绿色”化学药品的首个实例。