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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Bell, David S. Capitani, Donatella Campiglia, Pietro Kotoni, Dorina Villani, Claudio Gasparrini, Francesco |
| Description | Country affiliation: Italy Author Affiliation: Kotoni D ( Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, P.le Aldo Moro 5, 00185 Roma, Italy.) |
| Abstract | A rational approach for the design and preparation of two new 'Crab-like' totally synthetic, brush-type chiral stationary phases is presented. Enantiopure diamines, namely 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-ethylene-diamine were treated with 3-(triethoxysilyl)propyl isocyanate, to yield reactive ureido selectors that were eventually attached to unmodified silica particles through a stable, bidentate tether, through a facile two-step one-pot procedure. A full chemical characterization of the new materials has been obtained through solid-state NMR (both (29)Si and (13)C CPMAS) spectroscopy. Columns packed with the two Crab-like chiral stationary phases allow for different mechanisms of separation: normal phase liquid chromatography, reversed phase liquid chromatography and polar organic mode and show a high stability at basic pH values. In particular, the Crab-like column containing the 1,2-diphenyl-1,2-ethylene-diamine selector proved a promising candidate for the resolution of a wide range of racemates (including benzodiazepines, N-derivatized amino acids, and free carboxylic acids) both in normal phase and polar organic mode. An Hmin of 9.57 at a µsf of 0.80mm/s (corresponding to 0.8mL/min) was obtained through van Deemter analysis, based on toluene, for the Crab-like column with the 1,2-diphenyl-1,2-ethylene-diamine selector (250mm×4.6mm I.D.), with a calculated reduced height equivalent to a theoretical plate (h) of only 1.91. Finally, comparative studies were performed with a polymeric commercially available P-CAP-DP column in order to evaluate enantioselectivity and resolution of the Crab-like columns. |
| ISSN | 00219673 |
| Volume Number | 1297 |
| e-ISSN | 18733778 |
| Journal | Journal of Chromatography A |
| Language | English |
| Publisher | Elsevier |
| Publisher Date | 2013-07-05 |
| Publisher Place | Netherlands |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Chromatography, High Pressure Liquid Instrumentation Diamines Chemistry Urea Amino Acids Cyclohexylamines Magnetic Resonance Spectroscopy Models, Chemical Models, Molecular Naphthalenes Solvents Stereoisomerism Toluene Journal Article Research Support, Non-u.s. Gov't Discipline Analytical Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Medicine Analytical Chemistry Biochemistry |
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