title: Click N-benzyl iminodiacetic acid: novel silica-based tridentate zwitterionic stationary phase for hydrophilic interaction liquid chromatography.
abstract: Iminodiacetic acid (IDA) is dicarboxylic acid amine, which may produce stronger interaction with polar or charged compounds than bidentate α,β-amino acid. In this article, a novel type of tridentate zwitterionic HILIC stationary phase was prepared by covalently bonding N-benzyl IDA on silica gel via copper(I) catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition (CuAAC). The structure of this stationary phase and all related intermediates was confirmed by NMR, FT-IR, MS spectrum and elemental analysis. The new stationary phase showed good HILIC characteristics and high column efficiency (the theoretical plate number is up to 44000 plates m(-1) in the case of guanosine) in the application of separation of polar compounds, including organic acids, organic bases, as well as highly polar and hydrophilic compounds, such as cephalosporins and carbapenems. Most of them displayed good peak shape and selectivity.
authors.affiliation: School of Pharmacy, Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Yin
authors.affiliation: School of Pharmacy, Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Huihui
authors.initials: H
authors.lastname: Chai
authors.affiliation: School of Pharmacy, Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
authors.forename: Renhua
authors.initials: R
authors.lastname: Liu
authors.affiliation: School of Pharmacy, Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China. Electronic address: chuch@ecust.edu.cn.
authors.forename: Changhu
authors.initials: C
authors.lastname: Chu
authors.affiliation: Department of Chemistry and Physics, University of St. Thomas, Houston, TX 77006, USA.
authors.forename: John A
authors.initials: JA
authors.lastname: Palasota
authors.affiliation: Department of Chemistry and Physics, University of St. Thomas, Houston, TX 77006, USA.
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Cai
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001565:Benzoates / Q000302:isolation & purification; D015780:Carbapenems / Q000302:isolation & purification*; D002511:Cephalosporins / Q000302:isolation & purification*; D002853:Chromatography, Liquid / Q000379:methods*; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D057927:Hydrophobic and Hydrophilic Interactions; D007098:Imino Acids / Q000737:chemistry*; D011687:Purines / Q000302:isolation & purification; D011743:Pyrimidines / Q000302:isolation & purification; D058428:Silica Gel / Q000737:chemistry*; D012996:Solutions; D013411:Sulfadiazine / Q000302:isolation & purification
chemical_list: D000480:Alkynes; D001386:Azides; D001565:Benzoates; D015780:Carbapenems; D002511:Cephalosporins; D007098:Imino Acids; D011687:Purines; D011743:Pyrimidines; D012996:Solutions; D013411:Sulfadiazine; D058428:Silica Gel
keywords: Hydrophilic interaction chromatography; N-benzyl imino diacetic acid; Stationary phase; Zwitterionic