Lindqvist L, Jansson P E
Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institutet, Huddinge Hospital, Sweden.
J Chromatogr A. 1997 May 9;769(2):253-61. doi: 10.1016/s0021-9673(96)00987-9.
The absolute configuration of a sugar can be determined by gas-liquid chromatography of the acetylated or trimethylsilylated dithioacetals from 1-phenylethanethiol. The isolation of both enantiomers of 1-phenylethanethiol is also described. Using the acetates and both thiol reagents the absolute configuration of C-2 can be determined, provided it is a hydroxyl group, with great certainty. A new way of determining the absolute configuration of sugars, without references, is thereby provided. The sugars analysed include aldoses, deoxyaldoses, 2-acetamido-2-deoxyaldoses and uronic acids. The analysis is made using columns with non-chiral stationary phase and the electron impact mass spectra of the acetylated and trimethylsilylated bis(1-phenylethyl)dithioacetals are described.
糖的绝对构型可以通过对来自1-苯乙硫醇的乙酰化或三甲基硅烷基化二硫代缩醛进行气液色谱分析来确定。文中还描述了1-苯乙硫醇两种对映体的分离方法。使用乙酸酯和两种硫醇试剂，只要C-2位是羟基，就能非常确定地确定其绝对构型。由此提供了一种无需对照品就能确定糖绝对构型的新方法。所分析的糖包括醛糖、脱氧醛糖、2-乙酰氨基-2-脱氧醛糖和糖醛酸。分析采用非手性固定相柱，并描述了乙酰化和三甲基硅烷基化双(1-苯乙基)二硫代缩醛的电子轰击质谱。
