文献类型：期刊文献

中文题名：通过形成二酪氨酸酯酒石酸盐法制备D-酪氨酸的新方法

英文题名：Preparation of D-Tyrosine by Forming Tartaric Acid Dityrosine Ester Diastereomeric Salt

作者：彭阳峰[1];何佺[2];王家荣[2];高浩其[2];蔡水洪[1];田禾[3]

机构：[1]华东理工大学化工学院,上海200237;[2]宁波工程学院化工系,宁波315018;[3]华东理工大学精细化工研究所,上海200237

年份：2006

卷号：26

期号：1

起止页码：69

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;北大核心:【北大核心2004】；CSCD:【CSCD2011_2012】；

语种：中文

中文关键词：酪氨酸;酒石酸;拆分;酪氨酸甲酯;酪氨酸乙酯;二酪氨酸甲酯酒石酸盐

外文关键词：tyrosine; tartaric acid; resolution; tyrosine methyl ester; tyrosine ethyl ester; tartaric acid dityrosine methyl ester salt

摘要：研究了在乙醇溶液中光学活性L-酒石酸拆分DL-酪氨酸乙酯时的特性,发现溶液中同时存在着酒石酸、酪氨酸乙酯酒石酸氢盐和二酪氨酸乙酯酒石酸盐,三者之间的平衡关系影响拆分结果,所得酪氨酸的构型与L-酒石酸和DL-酪氨酸乙酯的投料摩尔比有关.前者的摩尔数大于后者时为富D-酪氨酸乙酯,小于后者时为富L-酪氨酸乙酯,两者相当时则得到DL-酪氨酸乙酯.进一步的研究探讨了D-酒石酸、L-酒石酸与L-酪氨酸乙酯在不同摩尔比下的成盐特性,从而解释了酒石酸拆分酪氨酸乙酯过程中的这一特性,说明由于二L-酪氨酸乙酯酒石酸盐和二D-酪氨酸乙酯酒石酸盐在乙醇中溶解度都很小,因此通过酒石酸拆分酪氨酸乙酯的方法不能得到高光学纯度的D-酪氨酸.在此基础上,通过形成二酪氨酸甲酯酒石酸盐的方法,在甲醇中成功地用D-酒石酸拆分制备了D-酪氨酸,光学纯度99%ee.
The characteristic of DL-tyrosine ethyl ester resolution by optically active L-tartaric acid in ethanol was researched. Tartaric acid, tartaric acid monotyrosine ethyl ester salt and tartaric acid dityrosine ethyl ester salt existed in ethanol solution simultaneously, and the equilibrium of the three materials played an important role in resolution results. The configuration of resolved tyrosine was affected by the molar ratio of L-tartaric acid to DL-tyrosine ethyl ester. If the former was more than the latter, more D-tyrosine was produced than L-tyrosine, but if the former was less than the latter, more L-tyrosine was produced, and if both were equal, racemic DL-tyrosine was produced. Deeper research on the characteristic of diastereomeric crystallization of D-tartaric acid, L-tartaric acid and L-tyrosine ethyl ester in different molar ratio, revealed the special property of this resolution process. Because of the low solubility of tartaric acid diL- or D-tyrosine ethyl ester salt in ethanol, the optically pure D-tyrosine could not be prepared through resolving tyrosine ethyl ester by tartaric acid. However, through forming the tartaric acid dityrosine methyl ester diastereomeric salt in methanol, the D-tyrosine was prepared successfully with 99.0% optical purity.