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Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds.
J Chromatogr A. 2011 Aug 12; 1218(32):5498-503.JC

Abstract

Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader.

Authors+Show Affiliations

Department of Chemistry, Box 9573, Mississippi State University, MS 39762, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

21741656

Citation

Dai, Zhi, et al. "Steric Effects On the Enantiodiscrimination of Diproline Chiral Stationary Phases in the Resolution of Racemic Compounds." Journal of Chromatography. A, vol. 1218, no. 32, 2011, pp. 5498-503.
Dai Z, Ye G, Pittman CU, et al. Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds. J Chromatogr A. 2011;1218(32):5498-503.
Dai, Z., Ye, G., Pittman, C. U., & Li, T. (2011). Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds. Journal of Chromatography. A, 1218(32), 5498-503. https://doi.org/10.1016/j.chroma.2011.06.047
Dai Z, et al. Steric Effects On the Enantiodiscrimination of Diproline Chiral Stationary Phases in the Resolution of Racemic Compounds. J Chromatogr A. 2011 Aug 12;1218(32):5498-503. PubMed PMID: 21741656.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds. AU - Dai,Zhi, AU - Ye,Guozhong, AU - Pittman,Charles U,Jr AU - Li,Tingyu, Y1 - 2011/06/21/ PY - 2011/02/02/received PY - 2011/06/01/revised PY - 2011/06/09/accepted PY - 2011/7/12/entrez PY - 2011/7/12/pubmed PY - 2011/9/29/medline SP - 5498 EP - 503 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1218 IS - 32 N2 - Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/21741656/Steric_effects_on_the_enantiodiscrimination_of_diproline_chiral_stationary_phases_in_the_resolution_of_racemic_compounds_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(11)00862-4 DB - PRIME DP - Unbound Medicine ER -