RESOLUTION OF THE ENANTIOMERS OF ALDOSES BY LIQUID-CHROMATOGRAPHY OF DIASTEREOISOMERIC 1-(N-ACETYL-ALPHA-METHYLBENZYLAMINO)-1-DEOXYALDITOL ACETATES
RESOLUTION OF THE ENANTIOMERS OF ALDOSES BY LIQUID-CHROMATOGRAPHY OF DIASTEREOISOMERIC 1-(N-ACETYL-ALPHA-METHYLBENZYLAMINO)-1-DEOXYALDITOL ACETATES
复制标题
DOI：
10.1016/s0008-6215(00)80536-4
复制
发表时间：
1982-01-01
影响因子：
3.1
通讯作者：
KUMANOTANI, J
中科院分区：
文献类型：
--
作者：
OSHIMA, R;YAMAUCHI, Y;KUMANOTANI, J
无环非对映异构体，即1-(N-乙酰基-α-甲基苄氨基)-1-脱氧糖醇乙酸酯，可以通过在氰基硼氢化钠存在下用手性α-甲基苄胺(MBA)还原胺化醛糖来容易地获得，并且可以通过反相液晶分离。 （液相色谱），更有效的是，通过吸附 L.C.根据该程序，可以解析常见的中性醛糖的对映体。在吸附LC中，对于赤藓糖、木糖、核糖、葡萄糖、4-O-甲基葡萄糖、半乳糖和岩藻糖，L-L*[定义为L-醛糖和L-(-)-MBA的加合物]在D-D*之前洗脱，对于阿拉伯糖、来苏糖、甘露糖、鼠李糖和甘油醛，洗脱顺序相反。这种行为可能与醛糖的 C-2 构型有关。
Acyclic diastereoisomers, namely, 1-(N-acetyl-.alpha.-methylbenzylamino)-1-deoxyalditol acetates, are readily obtained by reductive amination of aldoses with chiral .alpha.-methylbenzylamine (MBA) in the presence of sodium cyanoborohydride, and may be separated by reversed-phase l.c. (liquid chromatography) and, more effectively, by adsorption l.c. According to this procedure, enantiomers of the common, neutral aldoses are resolved. In adsorption l.c., L-L* [defined as an adduct of an L-aldose and L-(-)-MBA] is eluted before D-D* for erythrose, xylose, ribose, glucose, 4-O-methylglucose, galactose and fucose, and the elution order is the reverse for arabinose, lyxose, mannose, rhamnose and glyceraldehyde. This behavior is probably related to the configuration of C-2 of the aldoses.