Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized With L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides
Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized With L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides
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DOI：
10.1002/chir.22456
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发表时间：
2015-07-01
期刊：
影响因子：
2
通讯作者：
Kodama, Shuji
中科院分区：
文献类型：
--
作者：
Shou, Mirei;Terashima, Hiroyuki;Kodama, Shuji
三种己醛糖（葡萄糖、半乳糖和甘露糖）和三种戊醛糖（阿拉伯糖、木糖和核糖）在碱性条件下用 L-色氨酸酰胺 (L-TrpNH(2)) 衍生化。使用碱性流动相(pH9.2)，三种己醛糖或三种五醛糖分别同时对映分离，但所有六种单糖不能同时对映分离。单糖衍生后检测到大量未反应的L-TrpNH(2)。为了扩大分离窗口，可以通过用乙酸乙酯进行液-液萃取来消除大部分未反应的L-TrpNH(2)，并且发现使用中性流动相时衍生化单糖和未反应的L-TrpNH(2)的洗脱顺序相反。使用 InertSustainSwift C18 柱（4.6mm i.d. x 150mm）和含有 180mM 磷酸盐缓冲液（pH7.6）、1.5mM 丁基硼酸和 5% 乙腈的流动相，在 40 摄氏度下，通过反相高效液相色谱 (HPLC) 同时对所有六种单糖进行对映分离。单糖的 D 和 L 命名法基于戊醛糖的不对称 C4 中心和己醛糖的 C5 中心的构型。结果发现，该方法中这六种单糖和岩藻糖的对映体洗脱顺序符合C2中心的绝对构型。手性 27:417-421, 2015。(c) 2015 Wiley periodicals, Inc.
Three aldohexoses, glucose, galactose, and mannose, and three aldopentoses, arabinose, xylose, and ribose, were derivatized with L-tryptophanamide (L-TrpNH(2)) under alkaline conditions. Using a basic mobile phase (pH9.2), the three aldohexoses or the three aldopentoses were simultaneously enantioseparated, respectively, but all the six monosaccharides could not be simultaneously enantioseparated. A large amount of nonreacted L-TrpNH(2) was detected after the derivatized monosaccharides. In order to widen the separation window, a large portion of nonreacted L-TrpNH(2) could be eliminated by liquid-liquid extraction with ethylacetate, and elution order of the derivatized monosaccharides and nonreacted L-TrpNH(2) was found to be reversed using a neutral mobile phase. All of the six monosaccharides were simultaneously enantioseparated by reversed phase high-performance liquid chromatography (HPLC) using InertSustainSwift C18 column (4.6mm i.d. x 150mm) and a mobile phase containing 180mM phosphate buffer (pH7.6), 1.5mM butylboronic acid, and 5% acetonitrile at 40 degrees C. Nomenclature of D and L for monosaccharides is based on the configurations of the asymmetric C4 center for aldopentoses and C5 center for aldohexoses. It was found that the enantiomer elution order of these six monosaccharides and fucose in the proposed method conformed to be the absolute configuration of the C2 center. Chirality 27:417-421, 2015. (c) 2015 Wiley Periodicals, Inc.