Performance of brush-type HPLC chiral stationary phases with tertiary amide in the connecting tether

Chirality

Volumn 18, Issue 10, 2006, Pages 857-869

  Forjan, Davorka Moslavac ^a   Kontrec, Darko ^a   Vinković, Vladimir ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Chiral liquid chromatography; Electron rich shield; Enantiomer separation; Tertiary amide connecting tether

Indexed keywords

1 NAPHTHYL DERIVATIVE; 3,5 DIMETHYLPHENYL DERIVATIVE; ALANINE; ALIPHATIC COMPOUND; AMIDE; BASE; FUNCTIONAL GROUP; HYDROGEN; LEUCINE; N (3,5 DINITROBENZOYL)LEUCINE; NAPHTHYL GROUP; NITROGEN; PHENYL GROUP; SILICON DIOXIDE; TERTIARY AMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHIRALITY; ELECTRON; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; OPTICAL RESOLUTION; PERFORMANCE; PRIORITY JOURNAL; RACEMIC MIXTURE; SEPARATION TECHNIQUE; SURFACE CHARGE;

AMIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33750423061     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20329     Document Type: Article

References (33)

1. Bojarski J, Aboul-Enein HY, Ghanem A. What's new in chromatographic enantioseparations. Curr Anal Chem 2005;1:59-77.
2. Perrin SR, Pirkle WH. Commercially available brush-type chiral selectors for the direct resolution of enantiomers. In: Ahuja S, editor. Chiral Separations by Liquid Chromatography. (ACS Symposium Series No. 471). Washington, D.C.: American Chemical Society; 1991. pp 43-66.
3. Kern J, Kirkland K. Chiral separations. In: Snyder LR, Kirkland JJ, Glajch JL, editors. Practical HPLC Method Development. New York: Wiley; 1997. pp 585-588.
4. Pirkle WH, Pochapsky TC. Intermolecular proton [proton] nuclear Overhauser effects in diastereomeric complexes: Support for a chromatographically derived chiral recognition model. J Am Chem Soc 1986;108:5627,5628.
5. Pirkle WH, Pochapsky TC. Chiral molecular recognition in small bimolecular systems: A spectroscopic investigation into the nature of diastereomeric complexes. J Am Chem Soc 1987;109:5975-5982.
6. Pirkle WH, Burke JA, Wilson SR. X-ray crystallographic support of a chiral recognition model. J Am Chem Soc 1989;111:9222,9223.
7. Hyun MH, Min C-S, Cho YJ, Na MS. An improved chiral recognition model for resolving N-acyl-α-aryl-alkylamines on Pirkle-type π-acidic chiral stationary phases. J Liq Chromatogr 1995;18:2527-2541.
8. Götmar G, Fornstedt T, Guiochon G. Apparent and true enantioselectivity in enantioseparations. Chirality 2000;12:558-564.
9. Pirkle WH, Welch CJ, Bowen WE, Yang Q. US Patent 5, 422,004 (1995).
10. Pirkle WH, Welch CJ. Effect of superfluous remote polar functionality on chiral recognition. J Chromatogr A 1992;589:45-51.
11. Pirkle WH, Spence PL, Lamm B, Welch CJ. Doubly tethered tertiary amide selectors: Modified version of Doyle et al.'s naproxen chiral stationary phase. J Chromatogr A 1994;659:69-74.
12. Lee W. Effect of the amide connecting tether type of Pirkle-concept chiral stationary phases derived from (S)-N-(3,5-dinitrobenzoyl) leucine on enantiomeric separations. Anal Lett 1999;32:423-432.
13. Hyun MH, Lee JB, Kim YD. An improved (S)-leucine-derived π-acidic HPLC chiral stationary phase for the resolution of π-acidic racemates. J High Resolut Chromatogr 1998;21:69-71.
14. Gazić I, Kontrec D, Lesac A, Vinkovic V. The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid. Tetrahedron: Asymmetry 2005;16:1175-1182.
15. Pirkle WH, Hyun MH. A chiral stationary phase for the facile resolution of amino acids, amino alcohols and amines as the N-3,5-dinitrobenzoyl derivatives. J Org Chem 1984;49:3043-3046.
16. Pirkle WH, Murray PG, Burke JA. Use of homologous series of analytes as mechanistic probes to investigate the origins of enantioselectivity on two chiral stationary phases. J Chromatogr 1993;641: 21-29.
17. Pirkle WH, Alessi DM, Hyun MH, Pochapsky TC. Separation of some enantiomeric di- and tri- peptides on chiral stationary phases. J Chromatogr 1987;398:203-209.
18. Garrett CE, Jiang X, Prasad K, Repić O. New observations on peptide bond formation using CDMT. Tetrahedron Lett 2002;43:4161-4165.
19. Hyun MH, Na MS, Min C-S. Improved chiral stationary phase derived from (S)-naproxen for the liquid chromatographic resolution of enantiomers. J Chromatogr A 1996;732:209-214.
20. Hyun MH, Kim YD, Han SC. Design, preparation and application of a new π-basic chiral stationary phase for the liquid chromatographic separation of enantiomers. J High Resolut Chromatogr 2000;23:333-337.
21. Ranogajec A, Kontrec D, Vinković V, Šunjić V. Enantiomer separation and molecular recognition with new chiral stationary phases on 4-chloro-3,5-dinitrobenzoic acid amides of α,β- aminoalcohols and α-arylethylamines. J Liq Qchromatogr Rel Technol 2003;26:63-83.
22. Zafirova B, Landek G, Kontrec D, Šunjić V, Vinković V. Study of chromatographic enantioseparation of the esters of N-dinitrobenzoyl (N-DNB) and N-benzoyl (N-B) α-amino acids on novel chiral stationary phases containing structurally matching N-DNB and N-B-α-AA amides in the chiral selector. Croat Chem Acta 2004;77:573-579.
23. Kontrec D, Vinković V, Šepelj M, Šunjić V. Experiments and models in enantiorecognition chiral Pirkle-type stationary phases containing aromatic π-acid branching units. Croat Chem Acta 2004;77:31-51.
24. Hyun MH, Cho YJ, Ryoo J-J, Jyung KK, Heo GS. Preparation and application of an (S)-naproxen chiral stationary phase. J Chromatogr A 1995;696:173-183.
25. Comisso G, Sega A, Šunjić V. Synthesis, conformational studies and enantioselective homogeneous catalytic hydrogenation with CRC-PHOS and some congeners. Croat Chem Acta 1981;54:375-395.
26. Pirkle WH, Burke JA. Preparation of a chiral stationary phase from an α-amino phosphonate. Chirality 1989;1:57-62.
27. Hyun MH, Kim KJ, Jyung KK. Preparation of a new HPLC chiral stationary phase from (S)-naproxen and application in elucidating chiral recognition models. Bull Korean Chem Soc 1997;18:1085-1089.
28. Rosini C, Bertucci C, Pini D, Altemura P, Salvadori P. Cinchona alkaloids for preparing new, easily accessible chiral stationary phases. I. 11-(10,11-Dihydro-6′-methoxy-cinchonan-9-OL)-tiopropylsilanized silica. Tetrahedron Lett 1985;26:3361-3364.
29. Pirkle WH, House DW, Finn JM. Broad spectrum resolution of optical isomers using chiral high-performance liquid chromatographic bonded phases. J Chromatogr 1980;192:143-158.
30. Kuropka R, Müller B, Höcker H, Berndt H. Chiral stationary phases via hydrosilylation reaction of N-acryloylamino acids. I. Stationary phase with one chiral centre for high-performance liquid chromatography and development of a new derivatization pattern for amino acid enantiomers. J Chromatogr 1989;481:380-386.
31. Hyun MH, Kim YD, Han SC, Lee JB. A chiral recognition mechanism proposed for resolving π-acidic racemates on π-acidic chiral stationary phases derived from (S)-leucine. J High Resolut Chromatogr 1998;21:464-470.
32. Abatangelo A, Zanetti F, Navarini L, Kontrec D, Vinković V, Šunjić V. Enantiomerization of 3-carbethoxy-1,4-benzodiazepin-2- one: Combined chiral HPLC and spectroscopic study. Chirality 2001;14:12-17.
33. Chiral Application Guide V, Regis® Technologies, USA. Available at: www.registech.com.