Huang Junmin, Chen Hui, Li Tingyu
Department of Chemistry, Box 9573, Mississippi State University, Mississippi State, MS 39762, USA.
J Chromatogr A. 2006 Jan 13;1102(1-2):176-83. doi: 10.1016/j.chroma.2005.10.033. Epub 2005 Nov 2.
Several new stationary phases were prepared to study the structure-activity relationship of the chiral resolution of racemic 1,1'-bi-2-naphthol with a modified dipeptide Asn-Asn selector. The number of amino acid, the side chain protecting groups of the amino acid, and the Fmoc end-capping group all proved important for enantioselectivity. The linker also influenced enantioselectivity. Influence of the length of the linker appears to be related to the accessibility of chiral selectors. The bond through which the selector is attached to the linker proved important. Based on these results, it is postulated that hydrogen bonding interactions between one side chain amide group of one Asn and the oxygen on the backbone of another Asn with the two hydroxyl groups of the analyte play an important role in the resolution of racemic 1,1'-bi-2-naphthol with the modified dipeptide Asn-Asn selector.
制备了几种新型固定相，以研究用修饰的二肽天冬酰胺-天冬酰胺选择剂拆分外消旋1,1'-联-2-萘酚的手性拆分结构-活性关系。氨基酸的数量、氨基酸的侧链保护基团以及芴甲氧羰基封端基团均被证明对对映选择性很重要。连接基也影响对映选择性。连接基长度的影响似乎与手性选择剂的可及性有关。选择剂与连接基连接的键被证明很重要。基于这些结果，推测一个天冬酰胺的一个侧链酰胺基团与另一个天冬酰胺主链上的氧与分析物的两个羟基之间的氢键相互作用在用修饰的二肽天冬酰胺-天冬酰胺选择剂拆分外消旋1,1'-联-2-萘酚中起重要作用。
