Investigation of Peptoid Chiral Stationary Phases Terminated with N'-Substituted Phenyl-L-proline/leucine
[8] Haginaka, J. J. Chromatogr. A 2001, 906, 253.
polarity of the amide group via an inductive effect,
which caused that the test racemates characterized with
—OH or —NH— groups interacted with the terminal
motif of selector preferably through hydrogen bonding
interactions, therefore the contributions of peptoid chain
to chiral recognitions were lessened relatively.
[9] Millot, M. C. J. Chromatogr. B 2003, 797, 131.
[10] Haginaka, J. J. Chromatogr. B 2008, 875, 12.
[11] Armstrong, D. W.; DeMond, W. J. Chromatogr. Sci. 1984, 22, 411.
[12] Bressolle, F.; Audran, M.; Pham, T.-N.; Vallon, J.-J. J. Chromatogr.
B 1996, 687, 303.
[13] Armstrong, D. W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen,
J.-R. Anal. Chem. 1994, 66, 1473.
[14] Ekborg-Ott, K. H.; Kullman, J. P.; Wang, X.; Gahm, K.; He, L.;
Armstrong, D. W. Chirality 1998, 10, 627.
Conclusions
[15] Horne, W. S. Expert Opinion on Drug Discovery 2011, 6, 1247.
[16] Yoo, B.; Kirshenbaum, K. Curr. Opin. Chem. Biol. 2008, 12, 714.
[17] Armand, P.; Kirshenbaum, K.; Goldsmith, R. A.; Farr-Jones, S.;
Barron, A. E.; Truong, K. T. V.; Dill, K. A.; Mierke, D. F.; Cohen, F.
E.; Zuckermann, R. N.; Bradley, E. K. Proc. Natl. Acad. Sci. U. S. A.
1998, 95, 4309.
[18] Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.;
Bradley, E. K.; Truong, K. T. V.; Dill, K. A.; Cohen, F. E.;
Zuckermann, R. N. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 4303.
[19] Wu, C. W.; Kirshenbaum, K.; Sanborn, T. J.; Patch, J. A.; Huang, K.;
Dill, K. A.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc.
2003, 125, 13525.
[20] Blaschke, G. J. Liq. Chromatogr. 1986, 9, 341.
[21] Blaschke, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 13.
[22] Wu, H.; Liang, T.; Yin, C.; Jin, Y.; Ke, Y.; Liang, X. Analyst 2011,
136, 4409.
[23] Wu, H.; Su, X.; Li, K.; Yu, H.; Ke, Y.; Liang, X. J. Chromatogr. A
2012, 1265, 181.
[24] Payagala, T.; Wanigasekara, E.; Armstrong, D. Anal. Bioanal. Chem.
2011, 399, 2445.
[25] Okamoto, Y.; Aburatani, R.; Hatada, K. J. Chromatogr. A 1987, 389,
95.
[26] Chankvetadze, B.; Yashima, E.; Okamoto, Y. J. Chromatogr. A
1994, 670, 39.
[27] Chankvetadze, B.; Yashima, E.; Okamoto, Y. J. Chromatogr. A
1995, 694, 101.
Peptoid chiral stationary phases (CSPs) terminated
with L-proline and L-leucine amide were further inves-
tigated via introducing p-methyl and p-chloro substitu-
ents on the terminal phenyl group. The influence of
substituent on selectivity was found varied along with
the terminal amino acid and peptoid chain length. For
the short peptoid selectors containing only Nspe unit,
p-methyl substituent performed similarly with no sub-
stituent. In L-proline amide terminated CSPs, p-chloro
substituent resulted in weakest recognition ability while
in L-leucine amide terminated CSPs, it performed best.
Long peptoid selectors containing three Nspe units out-
performing the short ones demonstrated the important
role of peptoid chain in chiral recognition again. How-
ever, it was found that in longer CSPs terminated with
L-leucine amide, the terminal unsubstituted phenyl in-
stead showed the best selectivity; p-methylphenyl ex-
hibited no obvious superiority; p-chlorophenyl produced
comparable selectivity with unsubstituted phenyl with
only a few better separations. Overall, any structural
modification of CSP that may bring about more
non-enantioselective interactions between selectand and
selector is bad for chiral resolution.
[28] Chankvetadze, B.; Chankvetadze, L.; Sidamonidze, S.; Kasashima,
E.; Yashima, E.; Okamoto, Y. J. Chromatogr. A 1997, 787, 67.
[29] Okamoto, Y.; Noguchi, J.; Yashima, E. React. Funct. Polym. 1998,
37, 183.
References
[1] Francotte, E. R. J. Chromatogr. A 2001, 906, 379.
[2] Andersson, S. In Chiral Separation Techniques, Vol. 205, Ed.:
Subramanian, G., Wiley-VCH, Weinheim, 2007, p. 585.
[3] Pirkle, W. H.; Pochapsky, T. C. Chem. Rev. 1989, 89, 347.
[4] Hesse, G.; Hagel, R. Chromatographia 1973, 6, 277.
[5] Hesse, G.; Hagel, R. Justus Liebigs Ann. Chem. 1976, 6, 996.
[6] Ikai, T.; Okamoto, Y. Chem. Rev. 2009, 109, 6077.
[30] Chen, H.; Lu, X.; Gao, R.; Zhou, J.; Wang, Q. Chin. J. Chem. 2000,
18, 533.
[31] Gao, R.; Yang, H.; Huang, J.; Wang, Q. Chin. J. Chem. 1998, 16,
145.
[32] Wu, H.; Ji, S.; Yang, B.; Yu, H.; Jin, Y.; Ke, Y.; Liang, X. J. Sep.
Sci. 2012, 35, 351.
[33] Vaton-Chanvrier, L.; Oulyadi, H.; Combret, Y.; Coquerel, G.;
Combret, J. C. Chirality 2001, 13, 668.
[7] Allenmark, S. G.; Andersson, S. J. Chromatogr. A 1994, 666, 167.
(Lu, Y.)
Chin. J. Chem. 2012, 30, 2791—2797
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
2797