Enantioselective HPLC of potentially CNS-active acidic amino acids with a cinchona carbamate based chiral stationary phase

Chirality

Volumn 20, Issue 3-4, 2008, Pages 571-576

  Sardella, Roccaldo ^a   Lämmerhofer, Michael ^b   Natalini, Benedetto ^a   Lindner, Wolfgang ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

1 aminoindan 1, 5 dicarboxylic acid (AIDA); 2 (5 carboxy 3 methyl 2 thienyl) glycine (3 MATIDA); 4 carboxyphenylalanine (4 CPHE); Chiral separation; Chiral stationary phase; Chiralpak QN AX; HPLC; tert butylcarbamoylquinine

Indexed keywords

1 AMINO 1,5 INDANDICARBOXYLIC ACID; 2 (2' CARBOXY 3' PHENYLCYCLOPROPYL)GLYCINE; 2 (4 CARBOXY 5 METHYL 2 THIENYL)GLYCINE; 2 (5 CARBOXY 3 METHYL 2 THIENYL)GLYCINE; 4 CARBOXYPHENYLALANINE; AMINO ACID DERIVATIVE; AMMONIUM ACETATE; CARBAMIC ACID; METHANOL; QUININE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CENTRAL NERVOUS SYSTEM; CHIRALITY; CINCHONA; ENANTIOMER; ENANTIOSELECTIVITY; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PH; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SOLUTE;

EID: 39749116852     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20529     Document Type: Article

References (27)

1. 1 Lämmerhofer M, Lindner W. Quinine and quinidine derivatives as chiral selectors. I. Brush‐type chiral stationary phases for HPLC based on cinchonan carbamates and their application as chiral anion exchangers. J Chromatogr A 1996 ; 741: 33–48.
2. 2 Piette V, Lämmerhofer M, Bischoff K, Lindner W. HPLC Enantioseparation of N‐protected amino acids using non‐porous silica modified by a quinine carbamate as chiral stationary phase. Chirality 1997 ; 9: 157–161.
3. 3 Maier NM, Nicoletti L, Lämmerhofer M, Lindner W. Enantioselective anion exchangers based on cinchona alkaloid derived carbamates: influence of C8/C9‐stereochemistry on chiral recognition. Chirality 1999 ; 11: 522–528.
4. 4 Czerwenka C, Lämmerhofer M, Lindner W. Micro‐HPLC and standard‐size HPLC for the separation of peptide stereoisomers employing an ion‐exchange principle. J Pharm Biomed Anal 2003 ; 30: 1789–1800.
5. 5 Czerwenka C, Lämmerhofer M, Lindner W. Structure‐enantioselectivity relationships for the study of chiral recognition in peptide enantiomer separation on cinchona alkaloid‐based chiral stationary phases by HPLC: influence of the N‐terminal protecting group. J Sep Sci 2003 ; 26: 1499–1508.
6. 6 Hamase K, Morikawa A, Ohgusu T, Lindner W, Zaitsu K. Comprehensive analysis of branched aliphatic d‐amino acids in mammals using an integrated multi‐loop two‐dimensional column‐switching high‐performance liquid chromatographic system combining reversed‐phase and enantioselective columns. J Chromatogr A 2007 ; 1143: 105–111.
7. 7 Mandl A, Nicoletti L, Lämmerhofer M, Lindner W. Quinine versus carbamoylated quinine‐based chiral anion exchangers. A comparison regarding enantioselectivity for N‐protected amino acids and other chiral acids. J Chromatogr A 1999 ; 858: 1–11.
8. 8 Ilisz I, Berkecz R, Peter A. HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: a review. J Sep Sci 2006 ; 29: 1305–1321.
9. 9 Peter A, Toeroek R, Armstrong DW. Direct high‐performance liquid chromatographic separation of unusual secondary amino acids and a comparison of the performances of Chirobiotic T and TAG columns. J Chromatogr A 2004 ; 1057: 229–235.
10. 10 Berthod A, Liu Y, Bagwill C, Armstrong DW. Facile LC enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J Chromatogr A 1996 ; 731: 123–137.
11. 11 Armstrong DW, Liu Y, Ekborgott KH. A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations. Chirality 1995 ; 7: 474–497.
12. 12 Davankov VA. Chiral separation by HPLC using the ligand‐exchange principle. In: Gübitz G, Schmid MG, editors. Chiral separations: methods and protocols; Series title: Methods in molecular biology, Vol. 243. Totowa, NJ, USA: Humana Press ; 2004. p 207–215.
13. 13 Davankov VA. 30 Years of chiral ligand exchange. Enantiomer 2000 ; 5: 209–223.
14. 14 Natalini B, Sardella R, Macchiarulo A, Pellicciari R. Dynamic ligand‐exchange chiral stationary phase from S ‐benzyl‐(R)‐cysteine. Chirality 2006 ; 18: 509–518.
15. 15 Natalini B, Sardella R, Macchiarulo A, Natalini S, Pellicciari R. (S)‐(−)‐α,α‐di(2‐naphthyl)‐2‐pyrrolidinemethanol, a useful tool to study the recognition mechanism in chiral ligand‐exchange chromatography. J Sep Sci 2007 ; 30: 21–27.
16. 16 Shinbo T, Yamaguchi T, Nishimura K, Sugiura M. Chromatographic separation of racemic amino acids by use of chiral crown ether‐coated reversed‐phase packings. J Chromatogr 1987 ; 405: 145–153.
17. 17 Hyun MH, Cho YJ, Jin JS. Liquid chromatographic direct resolution of ‐amino acids on a chiral crown ether stationary phase. J Sep Sci 2002 ; 25: 648–652.
18. 18 Hyun MH, Kim DH, Cho YJ, Jin JS. Preparation and evaluation of a doubly tethered chiral stationary phase based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid. J Sep Sci 2005 ; 28: 421–427.
19. 19 Gika H, Lämmerhofer M, Papadoyannis I, Lindner W. Direct separation and quantitative analysis of thyroxine and triiodothyronine enantiomers in pharmaceuticals by high‐performance liquid chromatography. J Chromatogr B 2004 ; 800: 193–201.
20. 20 Pellicciari R, Luneia R, Costantino G, Marinozzi M, Natalini B, Jakobsen P, Kanstrup A, Lombardi G, Moroni F, Thomsen C. 1‐Aminoindan‐1,5‐dicarboxylic acid: a novel antagonist at phospholipase C‐linked metabotropic glutamate receptors. J Med Chem 1995 ; 38: 3717–3719.
21. 21 Natalini B, Marinozzi M, Bade K, Sardella R, Thomsen C, Pellicciari R. Preparative resolution of 1‐aminoindan‐1,5‐dicarboxylic acid (AIDA) by chiral ligand‐exchange chromatography. Chirality 2004 ; 16: 314–317.
22. 22 Costantino G, Marinozzi M, Camaioni E, Natalini B, Sarichelou I, Micheli F, Cavanni P, Noe C, Moroni F, Pellicciari R. Stereoselective synthesis and preliminary evaluation of (+)‐ and (−)‐3‐methyl‐5‐carboxy‐thien‐2‐yl‐glycine (3‐MATIDA): identification of (+)‐3‐MATIDA as a novel mGluR1 competitive antagonist. Farmaco 2004 ; 59: 93–99.
23. 23 Pellicciari R, Marinozzi M, Natalini B, Costantino G, Luneia R, Giorgi G, Moroni F, Thomsen C. Synthesis and pharmacological characterization of all sixteen stereoisomers of 2‐(2′‐Carboxy‐3′‐phenylcyclopropyl)glycine. Focus on (2 S,1′ S,2′ S,3′ R)‐2‐(2′‐Carboxy‐3′‐phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptor antagonist. J Med Chem 1996 ; 39: 2259–2269.
24. 24 Bicker W, Lämmerhofer M, Lindner W. Direct high‐performance liquid chromatographic assay for enantioselective and diastereoselective analysis of selected pyrethroic acids. J Chromatogr A 2004 ; 1035: 37–46.
25. 25 Lämmerhofer M, Maier NM, Lindner W. Chiral anion exchange type stationary phases based on cinchonan alkaloids: effective tool for the separation of the enantiomers of chiral acids. Am Lab 1998 ; 30: 71–78.
26. 26 Lämmerhofer M, Gyllenhaal O, Lindner W. HPLC enantiomer separation of a chiral 1,4‐dihydropyridine monocarboxylic acid. J Pharm Biomed Anal 2004 ; 35: 259–266.
27. 27 Natalini B, Marinozzi M, Sardella R, Macchiarulo A, Pellicciari R. Evaluation of the enantiomeric selectivity in the chiral ligand‐exchange chromatography of amino acids by a computational model. J Chromatogr A 2004 ; 1033: 363–367.