title: Solution-phase synthesis and evaluation of tetraproline chiral stationary phases.
abstract: A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs.
authors.affiliation: Department of Chemistry, Mississippi State University, Starkville, Mississippi, USA.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Dai
authors.forename: Guozhong
authors.initials: G
authors.lastname: Ye
authors.forename: Charles U
authors.initials: CU
authors.lastname: Pittman
authors.forename: Tingyu
authors.initials: T
authors.lastname: Li
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline; D015203:Reproducibility of Results; D060327:Solid-Phase Synthesis Techniques / Q000191:economics / Q000379:methods*; D012996:Solutions; D013237:Stereoisomerism
chemical_list: C496789:9-fluorenylmethoxycarbonyl; D005449:Fluorenes; D009842:Oligopeptides; D012996:Solutions; D011392:Proline