Preparation of cross-linked chitosan/glyoxal molecularly imprinted resin for efficient chiral resolution of aspartic acid isomers

Biochemical Engineering Journal

Volumn 51, Issue 3, 2010, Pages 140-146

  Monier, M ^a,b   Ayad, D M ^b   Wei, Y ^a   Sarhan, A A ^b  

^a DREXEL UNIVERSITY   (United States)

^b Mansoura University   (Egypt)

Author keywords

Aspartic acid; Chitosan; Molecular imprinting

Indexed keywords

ADSORPTION; BIOSYNTHESIS; CHITOSAN; ENANTIOSELECTIVITY; ISOMERS; MOLECULAR MODELING; MOLECULES; MORPHOLOGY; NEGATIVE IMPEDANCE CONVERTERS; POLYMERIZATION; SCANNING ELECTRON MICROSCOPY; STEREOCHEMISTRY; SURFACE MORPHOLOGY;

ADSORPTION CAPACITIES; ASPARTIC ACIDS; CROSS LINKED CHITOSAN; DILUTE AQUEOUS SOLUTION; MOLECULAR IMPRINTING; MOLECULAR IMPRINTING TECHNIQUES; MOLECULARLY IMPRINTED; OPERATIONAL CONDITIONS;

AMINO ACIDS;

ACETIC ACID; ASPARTIC ACID; CHITOSAN; GLYOXAL; RESIN; SOLVENT;

ADSORPTION; AQUEOUS SOLUTION; ARTICLE; CHIRALITY; CROSS LINKING; ENANTIOSELECTIVITY; EXTRACTION; ISOMER; MOLECULAR IMPRINTING; PH; PRIORITY JOURNAL; RACEMIC MIXTURE; SCANNING ELECTRON MICROSCOPE;

EID: 77955418067     PISSN: 1369703X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bej.2010.06.007     Document Type: Article

References (30)

1. Lehn J.M. Supramolecular chemistry-scope and perspectives molecules, supermolecules, and molecular devices. Angew. Chem. Int. Ed. Engl. 1988, 27:89-112.
2. Cram D.J. The design of molecular hosts, guests, and their complexes. Angew. Chem. Int. Ed. Engl. 1988, 27:1009-1020.
3. Pedersen C.J. The discovery of crown ethers. Angew. Chem. Int. Ed. Engl. 1988, 27:1021-1027.
4. Yoshida M., Hatate Y., Uezu K., Goto M., Furusaki S. Chiral-recognition polymer prepared by surface molecular imprinting technique. Colloids Surf. A: Physicochem. Eng. Asp. 2000, 169:259-269.
5. Wulff G. Molecular imprinting in cross-linked materials with the aid of molecular templates: a way towards artificial antibodies. Angew. Chem. Int. Ed. Engl. 1995, 34:1812-1832.
6. Mosbach K., Ramstom O. The emerging technique of molecular imprinting and its future impact on biotechnology. Biotechnology 1996, 14:163-170.
7. Wulff G., Sarhan A. The use of polymers with enzyme-analogous structures for the resolution of racemates. Angew. Chem. Int. Ed. Engl. 1972, 11:341-346.
8. Chen Y., Kele M., Quinones I., Sellergren B., Guiochon G. Influence of the pH on the behavior of an imprinted polymeric stationary phase-supporting evidence for a binding site model. J. Chromatogr. A 2001, 927:1-17.
9. Huang X., Zou H., Chen X., Luo Q., Kong L. Molecularly imprinted monolithic stationary phases for liquid chromatographic separation of enantiomers and diastereomers. J. Chromatogr. A 2003, 984:273-282.
10. Yu C., Mosbach K. Influence of mobile phase composition and crosslinking density on the enantiomeric recognition properties of molecularly imprinted polymers. J. Chromatogr. A 2000, 888:63-72.
11. Rachkov A., Minoura N. Towards molecularly imprinted polymers selective to peptides and proteins. The epitope approach. Biochim. Biophys. Acta 2001, 1544:255-266.
12. Guo T.Y., Xia Y.Q., Hao G.J., Song M.D., Zhang B.H. Adsorptive separation of hemoglobin by molecularly imprinted chitosan beads. Biomaterials 2004, 25:5905-5912.
13. Lee H.S., Hong J. Chiral and electrokinetic separation of amino acids using polypyrrole-coated adsorbents. J. Chromatogr. A 2000, 868:189-196.
14. Kumar M.N.V.R., Muzzarelli R.A.A., Muzzarelli C., Sashiwa H., Domb A.J. Chitosan chemistry and pharmaceutical perspectives. Chem. Rev. 2004, 104:6017-6084.
15. Jameela S.R., Jayakrishnan A. Glutaraldehyde crosslinked chitosan as a long acting biodegradable drug delivery vehicle: studies on the in vitro release of mitoxantrone and in vivo degradation of microspheres in rat muscle. Biomaterials 1995, 16:769-775.
16. Kim J.H., Kim J.H., Jegal J., Lee K.H. Optical resolution of α-amino acids through enantioselective polymeric membranes based on polysaccharides. J. Membr. Sci. 2003, 213:273-283.
17. Aburto J., Borgne S.L. Selective adsorption of dibenzothiophene sulfone by an imprinted and stimuli-responsive chitosan hydrogel. Macromolecules 2004, 37:2938-2943.
18. Xia Y.Q., Guo T.Y., Song M.D., Zhang B.H., Zhang B.L. Hemoglobin recognition by imprinting in semi-interpenetrating polymer network hydrogel based on polyacrylamide and chitosan. Biomacromolecules 2005, 6:2601-2606.
19. 2+ based on Penicillium chrysogenum. J. Chem. Technol. Biotechnol. 2005, 80:439-444.
20. Tan T.W., He X.J., Du W.X. Adsorption behaviour of metal ions on imprinted chitosan resin. J. Chem. Technol. Biotechnol. 2001, 76:191-195.
21. Mukoma P., Jooste B.R., Vosloo H.C.M. Synthesis and characterization of cross-linked chitosan membranes for application as alternative proton exchange membrane materials in fuel cells. J. Power Sources 2004, 136:16-23.
22. Monier M., Ayad D.M., Wei Y., Sarhan A.A. Adsorption of Cu(II), Co(II), and Ni(II) ions by modified magnetic chitosan chelating resin. J. Hazard. Mater. 2010, 177:962-970.
23. Yang Q., Dou F., Liang B., Shen Q. Studies of cross-linking reaction on chitosan fiber with glyoxal. Carbohydr. Polym. 2005, 59:205-210.
24. Gupta K.C., Jabrail F.H. Glutaraldehyde and glyoxal cross-linked chitosan microspheres for controlled delivery of centchroman. Carbohydr. Res. 2006, 341:744-756.
25. Sarhan A.A., Ayad D.M., Badawy D.S., Monier M. Phase transfer catalyzed heterogeneous N-deacetylation of chitin in alkaline solution. React. Funct. Polym. 2009, 69:358-363.
26. Chinard F.P. Photometric estimation of praline and ornithine. J. Biol. Chem. 1952, 199:91-95.
27. Panahi R., Vasheghani-Farahani E., Shojaosadati S.A. Separation of l-lysine from dilute aqueous solution using molecular imprinting technique. Biochem. Eng. J. 2007, 35:352-356.
28. Langmuir I. The adsorption of gases on plane surfaces of glass, mica and platinum. J. Am. Chem. Soc. 1918, 40:1361-1403.
29. Freundlich H.M.F. Over the adsorption in solution. Z. Phys. Chem. 1906, 57:385-471.
30. Tempkin M.J., Pyzhev V. Kinetics of ammonia synthesis on promoted iron catalysts. Acta Physiochim. URSS 1940, 12:217-222.