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J Chromatogr A. 2013 Jul 12;1298:152-6. doi: 10.1016/j.chroma.2013.05.035. Epub 2013 May 22.

Study of stereomeric peptoid chiral stationary phases containing different chiral side chains.

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  • 1Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.


In this study, we investigated six stereomeric peptoid chiral stationary phases (CSPs) successively combining N'-phenyl-proline amide, α-phenylethyl amine, 2-aminocyclohexyl phenylcarbamate and another α-phenylethyl amine under normal phase mode. CSPs 1-4 with R-S-(R,R)-S, R-S-(S,S)-S, R-R-(R,R)-R and R-R-(S,S)-R configuration exhibited much different enantiorecognition abilities. Overall, CSPs 1 and 2 performed better for the 55 analytes tested. CSP 5 with mixed selectors combined partial selectivities of CSPs 1 and 2. CSP 6 as enantiomeric counterpart of CSP 2 exhibited similar enantioseparation ability and reversal elution orders for analytes resolved. For several biaryl type analytes, CSP 6 even outperformed commercial Chiralpak AD-H and Chiralcel OD-H. Excellent resolution of 3,3'-diphenyl-2,2'-bi-1-naphthalol (VANOL) on CSP 6 illustrated its potential application in preparative enantioseparation. Eluting orders of enantiomers on stereomeric CSPs also provided us further insight into enantiorecognition of some analytes.

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