Crich David, Sana Kasinath
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
J Org Chem. 2009 Oct 2;74(19):7383-8. doi: 10.1021/jo901218g.
A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods.
描述了一种基于使用N-[9-(硫代甲基)-9H-芴-2-基]琥珀酰胺酸和交联氨甲基聚苯乙烯树脂合成肽基硫代酸的方法。该方法采用标准的Boc化学固相肽合成技术，结合侧链醇和胺的9-芴基甲氧基羰基保护以及侧链酸和硫醇的9-芴基甲基保护。用哌啶完成从树脂上的切割，哌啶还用于去除侧链保护基，并避免了通常与Boc化学固相肽合成树脂切割阶段相关的HF条件。根据成熟的方法，通过标准烷基化将如此得到的硫代酸高产率地转化为简单硫酯。
