Role of Nitrogen Lewis Basicity in Boronate Affinity Chromatography of Nucleosides

详细信息    查看全文

• 作者：Robin Tuytten ; Filip Lemiè ; re ; Eddy L. Esmans ; Wouter A. Herrebout ; Benjamin J. van der Veken ; Bert U. W. Maes ; Erwin Witters ; Russell P. Newton ; Ed Dudley
• 刊名：Analytical Chemistry
• 出版年：2007
• 出版时间：September 1, 2007
• 年：2007
• 卷：79
• 期：17
• 页码：6662 - 6669
• 全文大小：232K
• 年卷期：v.79,no.17(September 1, 2007)
• ISSN：1520-6882

文摘

Urinary modified nucleosides have a potential role ascancer biomarkers, and most of the methods used in theirstudy have utilized low-pressure phenylboronate affinitychromatography materials for the purification of the cis-diol-containing nucleosides. In this study, a boronateHPLC column was surprisingly shown not to trap thenucleosides as would be expected from experience withthe classic Affigel 601 resin but showed only partialselectivity toward cis-diol groups while other groupsexhibited better retention. In aprotic conditions, trappingof nucleosides was possible; however, the selectivitytoward cis-diol-containing compounds was lost with theLewis basicity of available nitrogens being the maindeterminant of retention. The experimental findings arecompared to and confirmed by DFT calculations.