title: Chiral stationary phases based on chitosan bis(methylphenylcarbamate)-(isobutyrylamide) for high-performance liquid chromatography.
abstract: A series of chitosan bis(methylphenylcarbamate)-(isobutyrylamide) derivatives were synthesized by carbamylating chitosan isobutyrylamide with different methylphenyl isocyanates. Then the prepared chitosan derivatives were coated onto 3-aminopropyl silica particles, resulting in a series of new chiral stationary phases (CSPs) for high-performance liquid chromatography. It was observed that the chiral recognition abilities of these coated-type CSPs depended very much on the substituents on the phenyl moieties of the chitosan derivatives, the eluent composition, as well as the structure of racemates. As a typical example, the eluent tolerance of the prepared CSP with the best enantioseparation ability was investigated in detail, and the results revealed that the CSP exhibited extraordinary solvent tolerance and could still work without significant loss in enantioseparation capability after being flushed with chloroform (100%), ethyl acetate (100%) and even THF/n-hexane (70/30, v/v), while the traditional coated-type CSPs based on the cellulose and amylose derivatives, such as cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and amylose tris(3,5-dimethylphenylcarbamate) (ADMPC), might be dissolved or highly swollen in these eluents. Therefore, the application of the resultant CSPs could address the problem of the dissolution and high swelling of traditional coated-type CSPs in some unusual eluents, broadening the possibility of eluent choice. In addition, a comparison of the prepared CSPs with the well known CDMPC- and ADMPC- based CSPs concerning the chiral recognition ability was also made. Separation performances achieved on the as-prepared CSPs in different eluents were found to be even superior to CDMPC- and ADMPC-based CSPs for the tested chiral compounds. In summary, we could safely draw the conclusion that the CSPs derived from chitosan isobutyrylamide derivatives were capable of excellent chiral recognition ability, and meanwhile possessed satisfactory eluent tolerance in a wider range of solvents.
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Sheng
authors.initials: S
authors.lastname: Tang
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Bin
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Chen
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China. Electronic address: zwbai@wit.edu.cn.
authors.forename: Zheng-Wu
authors.initials: ZW
authors.lastname: Bai
authors.affiliation: Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China.
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Huang
mesh_terms: D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D048271:Chitosan / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D017953:Isocyanates / Q000737:chemistry; D048448:Phenylcarbamates / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry* / Q000592:standards; D012822:Silicon Dioxide; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D017953:Isocyanates; D048448:Phenylcarbamates; D011108:Polymers; D012997:Solvents; C080033:Chiralpak AD; D012822:Silicon Dioxide; D000688:Amylose; D048271:Chitosan
keywords: Chiral recognition; Chiral stationary phase; Chitosan derivatives; Enantiomer separation; High-performance liquid chromatography