Literature DB >> 21741656

Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds.

Zhi Dai1, Guozhong Ye, Charles U Pittman, Tingyu Li.   

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 class="Chemical">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.
Copyright © 2011 Elsevier B.V. All rights reserved.

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Year:  2011        PMID: 21741656      PMCID: PMC3154017          DOI: 10.1016/j.chroma.2011.06.047

Source DB:  PubMed          Journal:  J Chromatogr A        ISSN: 0021-9673            Impact factor:   4.759


  14 in total

Review 1.  High-performance liquid chromatography chiral stationary phases based on low-molecular-mass selectors.

Authors:  F Gasparrini; D Misiti; C Villani
Journal:  J Chromatogr A       Date:  2001-01-12       Impact factor: 4.759

Review 2.  Chiral separations.

Authors:  A M Stalcup
Journal:  Annu Rev Anal Chem (Palo Alto Calif)       Date:  2010       Impact factor: 10.745

3.  Chiral separations: fundamental review 2010.

Authors:  Timothy J Ward; Karen D Ward
Journal:  Anal Chem       Date:  2010-06-15       Impact factor: 6.986

Review 4.  Enantioselective chromatography in drug discovery.

Authors:  Yingru Zhang; Dauh-Rurng Wu; David B Wang-Iverson; Adrienne A Tymiak
Journal:  Drug Discov Today       Date:  2005-04-15       Impact factor: 7.851

5.  Preparation and evaluation of proline-based chiral columns.

Authors:  Junmin Huang; Peng Zhang; Hui Chen; Tingyu Li
Journal:  Anal Chem       Date:  2005-05-15       Impact factor: 6.986

Review 6.  Recent advances in peptide chiral selectors for electrophoresis and liquid chromatography.

Authors:  Louis Bluhm; Junmin Huang; Tingyu Li
Journal:  Anal Bioanal Chem       Date:  2005-05-10       Impact factor: 4.142

7.  Molecular-length and chiral discriminations by beta-structural poly(L-alanine) on silica.

Authors:  Atsuomi Shundo; Toshihiko Sakurai; Makoto Takafuji; Shoji Nagaoka; Hirotaka Ihara
Journal:  J Chromatogr A       Date:  2005-05-06       Impact factor: 4.759

8.  Preparation and characterization of poly(l-phenylalanine) chiral stationary phases with varying peptide length.

Authors:  Kaname Ohyama; Kana Oyamada; Naoya Kishikawa; Yoshihito Ohba; Mitsuhiro Wada; Toshihide Maki; Kenichiro Nakashima; Naotaka Kuroda
Journal:  J Chromatogr A       Date:  2008-09-12       Impact factor: 4.759

9.  Evaluation of triproline and tri-alpha-methylproline chiral stationary phases: retention and enantioseparation associated with hydrogen bonding.

Authors:  Wenjian Lao; Jay Gan
Journal:  J Chromatogr A       Date:  2009-05-03       Impact factor: 4.759

10.  Improvement of proline enantioselective stationary phases by replacing the 9-fluorenylmethoxycarbonyl group.

Authors:  Junmin Huang; Hui Chen; Peng Zhang; Tingyu Li
Journal:  J Chromatogr A       Date:  2006-02-17       Impact factor: 4.759

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