Preparation and application of methylcalix[4]resorcinarene-bonded silica particles as chiral stationary phase in high-performance liquid chromatography

Chirality

Volumn 23, Issue 1 E, 2011, Pages

  Tan, Huey Min ^a   Soh, Shu Fang ^a   Zhao, Jia ^a   Yong, E L ^a   Gong, Yinhan ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

C methylcalix 4 resorcinarene; chiral separation; chiral stationary phase; high performance liquid chromatography

Indexed keywords

BENZENE DERIVATIVE; BROMOACETIC ACID; METHYLCALIX[4]RESORCINARENE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PRIORITY JOURNAL;

ACETIC ACIDS; BENZENE; CALIXARENES; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN BONDING; ISOMERISM; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PHARMACEUTICAL PREPARATIONS; PHENYLALANINE; RESORCINOLS; SILICON DIOXIDE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 80054967899     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20983     Document Type: Article

References (24)

1. Gong YH, Lee HK,. Application of cyclam-capped β-cyclodextrin-bonded silica particles as chiral stationary phase in capillary electrochromatography for enantiomeric separations. Anal Chem 2003; 75: 1348-1354. (Pubitemid 36397166)
2. Koester CJ, Moulik A,. Trends in environmental analysis. Anal Chem 2005; 77: 3737-3754.
3. Ong TT, Wang RQ, Muderawan IW, Ng SC,. Synthesis and application of mono-6-(3-methylimidazolium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride as chiral stationary phases for high-performance liquid chromatography and supercritical fluid chromatography. J Chromatogr A 2008; 1182: 136-140.
4. Park JW, Lee SY, Park KK,. Molecular recognition of organic ammonium ions by diaza-crown ether-modified β-cyclodextrin in aqueous media. Chem Lett 2000; 6: 594-595.
5. Zhong QQ, He LF, Beesley TE, Trahanovsky WS, Sun P, Wang CL, Armstrong DW,. Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography. J Chromatogr A 2006; 1115: 19-45.
6. Lee T, Lee W, Hyun MH, Park JH,. Enantioseparation of alpha-amino acids on an 18-crown-6-tetracarboxylic acid-bonded silica by capillary electrochromatography. J Chromatogr A 2010; 1217: 1425-1428.
7. Ananchenko GS, Udachin KA, Coleman AW, Polovyanenko DN, Bagryanskaya EG, Ripmeester JA,. Crystalline inclusion complex of a calixarene with a nitroxide. Chem Commun 2008; 2: 223-225. (Pubitemid 350294111)
8. Liu Y, Li CJ, Guo DS, Pan ZH, Li Z,. A comparative study of complexation of beta-cyclodextrin, calix[4]arenesulfonate and cucurbit[7]uril with dye guests: fluorescence behavior and binding ability. Supramol Chem 2007; 19: 517-523.
9. Hu K, Tian YL, Yang H, Zhang JQ, Xie J, Ye BX, Wu YJ, Zhang SS,. Preparation and characterization of p-tert-butylcalix[4]arene modified sol-gel column for open-tubular capillary electrochromatography. J Liq Chromatogr Rel Technol 2009; 32: 2627-2641.
10. Healy LO, McEnery MM, McCarthy DG, Harris SJ, Glennon JD,. Silica-bonded calixarenes in chromatography: enantioseparations on molecular basket phases for rapid chiral LC. Anal Lett 1998; 31: 1543-1551. (Pubitemid 28329597)
11. Yakovenko AV, Boyko VI, Kalchenko VI, Baldini L, Casnati A, Sansone F, Ungaro R,. N-linked peptidocalix[4]arene bisureas as enantioselective receptors for amino acid derivatives. J Org Chem 2007; 72: 3223-3231. (Pubitemid 46668122)
12. Thamarai Chelvi SK, Yong EL, Gong YH,. Preparation and evaluation of calix[4]arene-capped β-cyclodextrin-bonded silica particles as chiral stationary phase for high-performance liquid chromatography. J Chromatogr A 2008; 1203: 54-58.
13. Thamarai Chelvi SK, Yong EL, Gong YH,. Application of bromoacetate-substituted β-CD-bonded silica particles as chiral stationary phase for HPLC. J Sep Sci 2010; 33: 74-78.
14. Sokoliess T, Menyes U, Roth U, Jira T,. Separation of cis- and trans-isomers of thioxanthene and dibenz[b,e]oxepin derivatives on calixarene- and resorcinarene-bonded high-performance liquid chromatography stationary phases. J Chromatogr A 2002; 948: 309-313.
15. Zheng SL, Coppens P,. Emission quenching of photoactive molecules embedded in supramolecular solids: synthesis, structure and photoluminescence studies of benzil in a CMCR-based inclusion complex with a saturated linker molecule. CrystEngComm 2005; 7: 289-293. (Pubitemid 40727415)
16. Ma BQ, Coppens P,. Transformation of a C-methylcalix[4]resorcinarene- based host-guest complex from a wave-like to a novel triangular brick-wall architecture. Chem Commun 2003; 4: 504-505. (Pubitemid 36246373)
17. Ma BQ, Zhang YG, Coppens P,. Multiple conformations of benzil in resoreinarene-based supramolecular host matrixes. J Org Chem 2003; 68: 9467-9472. (Pubitemid 37456520)
18. Ruderisch A, Iwanek W, Pfeiffer J, Fischer G, Albert K, Schurig V,. Synthesis and characterization of a novel resorcinarene-based stationary phase bearing polar head groups for use in reversed-phase high-performance liquid chromatography. J Chromatogr A 2005; 1095: 40-49. (Pubitemid 41566492)
19. Gong YH, Xue GP, Bradshaw JS, Lee ML, Lee HK,. Synthesis of crown ether-capped 3-(β-cyclodextrin)-2-hydroxypropylsilyl-appended silica particles for use as chiral stationary phases in chromatography. J Heterocycl Chem 2001; 38: 1317-1323.
20. Nishikubo, T., Kameyama, A., Tsutsui, K., Iyo, M,. Synthesis and photochemical reaction of novel p-alkylcalix[n]arene derivatives containing cationically polymerizable groups. J Polym Sci Part A Polym Chem 1999; 37: 1805-1814.
21. Ruderisch A, Sailer H, Schurig V, Kern DP,. Studies on sensitivity and etching resistance of calix[4]arene derivatives as negative tone electron beam resists. Microelectron Eng 2003; 67-68: 292-299.
22. Gong YH, Lee HK,. Application of naphthylcarbamate-substituted β-cyclodextrin-bonded silica particles as stationary phase for high-performance liquid chromatography. J Sep Sci 2003; 26: 515-520. (Pubitemid 36705593)
23. Liu M, Da SL, Feng YQ, Li LS,. Study on the preparation method and performance of a new β-cyclodextrin bonded silica stationary phase for liquid chromatography. Anal Chim Acta 2005; 533: 89-95. (Pubitemid 40354279)
24. Sokoliess T, Opolka A, Menyes U, Roth U, Jira T,. Separation of racemic drugs on chiral resorcinarene-bonded HPLC-columns. Pharmize 2002; 57: 589-590.