Resolution of racemic mixture of α-amino acid derivative through composite membrane

Journal of Membrane Science

Volumn 378, Issue 1-2, 2011, Pages 531-540

  Singh, Kripal ^a   Ingole, Pravin G ^a   Chaudhari, Jayesh ^a   Bhrambhatt, Harshad ^a   Bhattacharya, Amit ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Enantioselective membrane; Lysine hydrochloride; Optical resolution; Piperazine; Trimesoyl chloride

Indexed keywords

ENANTIOSELECTIVE MEMBRANE; LYSINE HYDROCHLORIDE; OPTICAL RESOLUTION; PIPERAZINE; TRIMESOYL CHLORIDE;

AMINO ACIDS; CHIRALITY; CHLORINE COMPOUNDS; COMPOSITE MEMBRANES; COPYING; ENANTIOMERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NANOCOMPOSITE FILMS; PRESSURE EFFECTS; SCANNING ELECTRON MICROSCOPY;

MEMBRANES;

LYSINE; NANOCOMPOSITE; PIPERAZINE; POLYSULFONE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOMER; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; MEMBRANE PERMEABILITY; MEMBRANE STRUCTURE; MORPHOLOGY; POLYMERIZATION; PRESSURE; PRIORITY JOURNAL; RACEMIC MIXTURE; SCANNING ELECTRON MICROSCOPY; SEPARATION TECHNIQUE; SURFACE PROPERTY;

EID: 79959975436     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2011.05.049     Document Type: Article

References (39)

1. Daniels J.M., Nestmann E.R., Kerr A. Development of stereoisomeric (chiral) drugs: a brief review of scientific and regulatory considerations. J. Drug Inf. 1997, 31:639-646.
2. McConathy J., Owens M.J. Stereochemistry in drug action. J. Clin. Psychiatry 2003, 5:70-73.
3. Jacques J., Collet A. Enantiomers, Racemates and Resolutions 1981, Wiley Interscience, New York. 2nd ed.
4. Food and Drug Administration, policy statement for the development of new stereoisomeric drugs, 57 Fed. Reg. 22 (1992) 249.
5. Subramanian G. Chiral Separation Techniques: A Practical Approach 2001, Wiley-VCH, New York. 2nd ed.
6. Bartsch R.A., Way J.D. Chemical separations with liquid membranes. Am. Chem. Soc. 1996, 642.
7. Osada Y., Ohta F., Mizumoto A., Takase M., Kurimura Y. Specific permeation and adsorption of aqueous amino acids by plasma-polymerized membranes of d-camphor and l-menthol. J. Chem Soc. Jpn. 1986, 7:p866.
8. Maruyama A., Adachim N., Takatsuki T., Torii M., Sanui K., Ogata N. Enantioselective permeation of (-amino acids isomers through poly(amino acid)-derived membranes. Macromolecules 1990, 23:2748-2752.
9. Tone S., Masawaki T., Hamada I. The optical resolution of amino acids by ultrafiltration membranes fixed with plasma polymerized l-menthols. J. Membr. Sci. 1995, 103:57-63.
10. Xiao Y., Chung Tai-S. Functionalization of cellulose dialysis membranes for chiral separation using β-cyclodextrin immobilization. J. Membr. Sci. 2007, 290:78-85.
11. Kakuchi T., Takaoka T., Yokota K. Polymeric chiral crown ethers VI optical resolution of α-amino acid by polymers incorporating 1,3-; 4,6-di-O-benzylidene-d-mannitol residues. Polym. J. 1990, 22:199-205.
12. Thoelen C., De bruyn M., Theunisse E., Vankelecom I.F.J., Yoshikawa M., Jacobs P.A. Membranes based on poly (γ-methyl-l-glutamate): synthesis, characterization and use in chiral separations. J. Membr. Sci. 2001, 186:153-163.
13. Xiong W.W., Wang W.F., Zhao L., Song Q., Yuan L.M. Chiral separation of (R,S)-2-phenyl-1-propanol through glutaraldehyde-crosslinked chitosan membranes. J. Membr. Sci. 2009, 328:268-272.
14. Higuchi A., Hara M., Horiuchi T., Nakagawa T. Optical resolution of amino acids by ultrafiltration membranes containing serum albumin. J. Membr. Sci. 1994, 93:157-164.
15. Singh K., Bajaj H.C., Ingole P., Bhattacharya A. Comparative study of enantioseparation of racemic tryptophan by ultrafiltration using BSA-immobilized and BSA-interpenetrating network polysulfone membranes. Sep. Sci. Technol. 2010, 45:346-354.
16. Yashima E., Noguchi J., Okamoto Y. Enantiomer enrichment of oxprenolol through cellulose tris(3,5-dimethylphenylcarbamate) membrane. J. Appl. Polym. Sci. 1994, 54:1087-1091.
17. Xie S.M., Wang W.F., Ai P., Yang M., Yuan L.M. Chiral separation of (R,S)-2-phenyl-1-propanol through cellulose acetate butyrate membranes. J. Membr. Sci. 2008, 321:293-298.
18. Zhao M., Xu X.L., Jiang Y.D., Sun W.Z., Wang W.F., Yuan L.M. Enantioseparation of trans-stilbene oxide using a cellulose acetate membrane. J. Membr. Sci. 2009, 336:149-153.
19. Aoki T., Shinohara K., Oikawa E. Optical resolution through the solid membrane from (+)-poly{1-[dimethyl(10-pinanyl)-silyl]-1-propyne}. Makromol. Chem. Rapid Commun. 1992, 13:565-570.
20. Aoki T., Tomizawa S., Oikawa E. Enantioselective permeation through poly {γ-[3-pentamethyldisiloxanyl) propyl]-l-glutamate} membranes. J. Membr. Sci. 1995, 99:117-125.
21. Aoki T., Maruyama A., Shinohara K., Oikawa E. Optical resolution by use of surface modified poly(methyl methacrylate) membrane containing (-)-oligo(methyl(10-pinanyl) siloxane). Polym. J. 1995, 27:547-550.
22. Aoki T., Shinohara K., Oikawa E. Optical resolution by vapor permeation of 1,3-butanediol and 2-butanol through (+)-poly{1-[dimethyl(10-pinanyl)silyl]-1-propyne} membranes. Polymer 1995, 36:2403-2405.
23. Aoki T., Shinohara K., Kaneko T., Oikawa E. Enantioselective permeation of various racemates through an active poly{1-[dimethyl (10-pinanyl)silyl]-1-propyne} membranes. Macromolecules 1996, 29:4192-4198.
24. Aoki T., Kaneko T., Oikawa E. Synthesis and enantioselective of chiral poly(phenylene-ethylene)s bearing bulky optically active methyl groups. Polymer 2001, 42:351-355.
25. Aoki T. Macromolecular design of perm-selective membranes. Prog. Polym. Sci. 1999, 24:951-993.
26. Xie R., Chu L.Y., Deng J.G. Membranes and membrane processes for chiral resolution. Chem. Soc. Rev. 2008, 37:1243-1263.
27. Petersen R., Cadotte J. Thin Film Composite Reverse Osmosis Membranes, Handbook of Industrial Membrane Technology 1990, 307-348. Noyes Publications, Park Ridge, NJ. M. Portr (Ed.).
28. Mulder M. Basic Principles of Membrane Technology 1997, Kluwer Academic Publishers, pp. 123-129.
29. Nobel R.D. Membrane Separation Technology - Principle and Applications 2003, Elsevier. 3rd ed.
30. Technical note on FTIR spectroscopy PerkinElmer Life and Analytical Sciences 710 Bridgeport Avenue Shelton. http://www.perkinelmer.com/.
31. Marek W. Urban, Attenuated Total Reflectance Spectroscopy of Polymers: Theory and Practice (Polymer Surfaces and Interfaces Series), American Chemical Society, 1996.
32. Darcy H. Les Fontaines Publiques de le Ville deDijon 1956, Victor Delmont, Paris.
33. Kim A.S., Chen H. Diffusive tortuosity factor of solid and soft cake layers: a random walk simulation approach. J. Membr. Sci. 2006, 279:129-139.
34. Hadik P., Szabbb L.P., Nagy E. d,l-Lactic acid and d,l-alanine enantioseparation by membrane process. Desalination 2002, 148:193-198.
35. Williams M.E. A Review of Reverse Osmosis Theory 2003, EET Corporation and Williams Engineering Services Company, Inc.
36. Aminabhavi T.M., Aithal U.S., Shukla S.S. An overview of the theoretical models used to predict transport of small molecules through polymer membranes. J. Macromol. Sci. - Rev. Macromol. Chem. Phys. 1988, C28(3&4):421-474.
37. Bhattacharyya D., Jevtitch M., Schrodt J., Fairweather G. Prediction of membrane separation characteristics by pore distribution measurements and surface force-pore flow model. Chem. Eng. Commun. 1986, 42:111-128.
38. Wijmans J.G., Baker R.W. The solution diffusion model: a review. J. Membr. Sci. 1995, 107:1-21.
39. Bowen W.R., Mukhtar H. Characterization and prediction of separation performance of nanofiltration membranes. J. Membr. Sci. 1996, 112:263-274.