Chiral separation performance of micrometer-sized monodispersed silica spheres with high protein loading

Chirality

Volumn 21, Issue 8, 2009, Pages 760-768

  Zhai, Zheng ^a   Chen, Yang ^a   Wang, Yu Jun ^a   Luo, Guang Sheng ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

Amino acid; Bovine serum albumin (BSA); Enantioseparation; Monodispersed silica spheres; Protein loading

Indexed keywords

ADSORBENT; PHENYLALANINE; SILICON DIOXIDE; TRYPTOPHAN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ELECTRON MICROSCOPY; ENANTIOMER; INFRARED SPECTROSCOPY; MATERIAL STATE; PARTICLE SIZE; PRIORITY JOURNAL;

ABSORPTION; ADSORPTION; ANIMALS; CATTLE; CHEMISTRY, ANALYTICAL; MICROCHEMISTRY; MICROSCOPY, ELECTRON, SCANNING; MICROSPHERES; PHENYLALANINE; SERUM ALBUMIN, BOVINE; SILICON DIOXIDE; STEREOISOMERISM; TRYPTOPHAN;

EID: 70349559105     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20677     Document Type: Article

References (35)

1. Gerald G, Martin GS. Chiral separation by chromatographic and electromigration techniques. A review. Biopharm Drug Dispos 2001;22: 291-336.
2. Allenmark S, Bomgren B, Borén H. Direct resolution of enantiomers by liquid affinity chromatography on albumin-agarose under isocratic conditions. J Chromatogr A 1982;237:473-477.
3. Allenmark S. Enantioselective binding of small ligands to proteins and its use for direct separation of optical antipodes by isocratic liquid affinity chromatography. Chem Scripta 1982;20(1-2):5-10.
4. Allenmark S. Optical resolution by liquid chromatography on immobilized bovine serum albumin. J Liq Chromatogr 1986;9(2-3):425.
5. Nakamura M, Kiyohara S, Saito K, Sugita K, Sugo T. Chiral separation of DL-tryptophan using porous membranes containing multilayered bovine serum albumin crosslinked with glutaraldehyde. J Chromatogr A 1998;822:53-58.
6. Kiyohara S, Nakamura M, Saito K, Sugita K, Sugo T. Binding of DL-tryptophan to BSA adsorbed in multilayers by polymer chains grafted onto a porous hollow-fiber membrane in a permeation mode. J Membr Sci 1999;152:143-149.
7. Haginaka J, Seyama C, Kanasugi N. The absence of chiral recognition ability in ovomucoid: ovoglycoprotein-bonded HPLC Stationary phases for chiral recognition. Anal Chem 1995;67:2539-2547.
8. 1-acid glycoprotein by fluorescence spectrophotometry. J Photochem Photobiol B: Biol 2007; 86:246-251.
9. Haginaka J, Seyama C, Murashima T. Retentive and enantioselective properties of ovomucoid-bonded silica columns. Influence of protein purity and isolation method. J Chromatogr A 1995;704:279-287.
10. Fagerström A, Nilsson M, Berg U, Isaksson R. PH dependency of ligand binding to cellobiohydrolase 1 (Cel7A): affinity, selectivity and inhibition for designed propranolol analogues. J Chromatogr A 2007;1138(1-2):276-283.
11. Okamoto Y, Ikawa Y, Kitagawa F, Otsuka K. Preparation of fritless capillary using avidin immobilized magnetic particles for electrochromatographic chiral separation. J Chromatogr A 2007;1143(1-2):264-269.
12. Han NY, Hautala JT, Bo T, Wiedmer SK, Riekkola M-L. Immobilization of phospholipid-avidin on fused-silica capillaries for chiral separation in open-tubular capillary electrochromatography. Electrophoresis 2006;27:1502-1509.
13. Wainer IW, Jadaud P, Schombaum GR, Kadodkar SV, Henry MP. Enzymes as HPLC stationary phases for chiral resolutions: initial investigations with α-chymotrypsin. Chromatographia 1988;25:903-907.
14. Wei Y, Zhao GF, Dong XY, Sun Y. High-capacity purification of hen egg-white proteins by ion-exchange electrochromatography with an oscillatory transverse electric field. J Sep Sci 2006;29:2383-2389.
15. Millot MC. Separation of drug enantiomers by liquid chromatography and capillary electrophoresis, using immobilized proteins as chiral selectors. J Chromatogr B 2003;797(1-2):131-159.
16. Harada K, Yuan Q, Nakayama M, Sugii A. Effects of organic modifiers on the chiral recognition by different types of silica-immobilized bovine serum albumin. J Chromatogr A 1996;740:207-213.
17. Wännman H, Walhagen A, Erlandsson P. Practical approach to the miniaturization of chiral separations in liquid chromatography using packed fused-silica capillary columns. J Chromatogr A 1993;603(1-2): 121-131.
18. Erlandsson P, Nilsson S. Use of a fragment of bovine serum albumin as a chiral stationary phase in liquid chromatography. J Chromatogr A 1989;482:35-51.
19. Andersson S, Allenmark S, Erlandsson P, Nilsson S. Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases. VIII. A comparison of a series of sorbents based on bovine serum albumin and its fragments. J Chromatogr A 1990; 498:81-91.
20. Park JH, Ryu JK, Park JK, McNeff CV, Carr PW. Separation of enantiomers on bovine serum albumin coated zirconia in reversed-phase liquid chromatography. Chromatographia 2001;53(7-8):405-408.
21. Li T, Yu QW, Lin B, Feng YQ. Synthesis and chromatographic properties of a chiral stationary phase derived from bovine serum albumin immobilized on magnesia-zirconia using phosphonate spacers. J Sep Sci 2007;30:804-812.
22. Yiu HHP, Wright PA. Enzymes supported on ordered mesoporous solids: a special case of an inorganic-organic hybrid. J Mater Chem 2005;15(35-36):3690-3700.
23. Loun B, Hage DS. Chiral separation mechanisms in protein-based HPLC columns, Part 1: Thermodynamic studies of (R)-warfarin and (S)-warfarin binding to immobilized human serum-albumin. Anal Chem 1994;66:3814-3822.
24. Loun B, Hage DS. Chiral separation mechanisms in protein-based HPLC columns, Part 2: Kinetic studies of (R)- and (S)-warfarin binding to immobilized human serum albumin. Anal Chem 1996;68:1218-1225.
25. Kato M, Sakai-Kato K, Matsumoto N, Toyo'oka T. A protein-encapsulation technique by the sol-gel method for the preparation of monolithic columns for capillary electrochromatography. Anal Chem 2002;74: 1915-1921.
26. Millot MC, Taleb NL, Sebille B. Binding of human serum albumin to silica particles by means of polymers: a liquid chromatographic study of the selectivity of resulting chiral stationary phases. J Chromatogr B 2002;768:157-166.
27. Millot MC, Sebille B, Mangin C. Enantiomeric properties of human albumin immobilized on porous silica supports coated with polymethacryloyl chloride. J Chromatogr A 1997;776:37-44.
28. Taleb NL, Millot MC, Sebille B. Enantioselectivity properties of human serum albumin immobilized on anion-exchangers based on polyvinylimidazole-coated silica. Effect of protein loading on separation properties. J Chromatogr A 1997;776:45-53.
29. Wang PC, Gao J, Lee CS. High-resolution chiral separation using microfluidics-based membrane chromatography. J Chromatogr A 2002;942(1-2):115-122.
30. Kato M, Matsumoto N, Sakai-Kato K, Toyo'oka T. Investigation of chromatographic performances and binding characteristics of BSA-encapsulated capillary column prepared by the sol-gel method. J Pharm Biomed Anal 2003;30:1845-1850.
31. Haginaka J, Takehira H. Separation of enantiomers on a chiral stationary phase based on ovoglycoprotein. I. Influence of the pore size of base silica materials and bound protein amounts on chiral resolution. J Chromatogr A 1997;773:85-91.
32. Chen Y, Wang YJ, Yang LM, Luo GS. Micrometer-sized monodisperse silica spheres with advanced adsorption properties. AIChE J 2008;54:298-309.
33. Andrew P, Mary TG. Applications of high performance liquid chromatography. New York: Wiley; 1979. 32 p.
34. Chen Y, Lv YC, Qi X, Luo GS. Mechanism and model of chiral separation of tryptophan by ultrafiltration using BSA (I). J Chem Ind Eng (China) 2007;58:114-118.
35. Qi X, Lv YC, Chen Y, Luo GS. Mechanism and model of chiral separation of tryptophan by ultrafiltration using BSA (II). J Chem Ind Eng (China) 2007;58:119-124.