IBMM, UMR-CNRS-5247, Universités Montpellier I and II, Place Eugène Bataillon, 34095 Montpellier, France.
Amino Acids. 2013 Aug;45(2):301-7. doi: 10.1007/s00726-013-1492-2. Epub 2013 Apr 26.
A new and efficient synthesis of (L)-(trimethylsilyl)alanine (TMSAla) with suitable protection for use in Solid Phase Peptide Synthesis (SPPS) has been accomplished starting from glycine tert-butyl ester and using hydroxypinanone as chiral inductor. The silylated side chain was introduced by alkylation of the Schiff base intermediate with iodomethyl(trimethylsilane) at -78 °C. Among the different synthetic routes that were tested including several chiral inductors and different Schiff bases, this strategy was selected and afforded (L)-TMSAla in good chemical overall yield with 98 % ee.
已完成一种新的、高效的（L）-（三甲基硅基）丙氨酸（TMSAla）的合成，该方法从叔丁基甘氨酸开始，使用羟基频哪酮作为手性诱导剂，为固相肽合成（SPPS）提供合适的保护。硅烷基侧链是通过希夫碱中间体与碘甲基（三甲基硅烷）在-78°C 下进行烷基化反应引入的。在所测试的不同合成路线中，包括几种手性诱导剂和不同的希夫碱，选择了这种策略，并以 98%ee 的高化学总收率得到了（L）-TMSAla。
