Effect of constituting amino acid residue numbers on molecularly imprinted chiral recognition sites

Chirality

Volumn 15, Issue 6, 2003, Pages 498-503

  Kondo, Yoshiko ^a   Morita, Yukihiro ^a   Fujimoto, Atushi ^a   Tounai, Masahiko ^a   Kimura, Satoshi ^a   Yoshikawa, Masakazu ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Chiral recognition; Molecular imprinting; Molecular recognition; Oligopeptide; Optical resolution

Indexed keywords

AMINO ACID; OLIGOPEPTIDE; TETRAPEPTIDE;

ADSORPTION; AMINO ACID SEQUENCE; ARTICLE; CHIRALITY; MOLECULAR IMPRINTING; MOLECULAR RECOGNITION; OPTICAL RESOLUTION; PRIORITY JOURNAL; RACEMIC MIXTURE;

AMINO ACIDS; MOLECULAR CONFORMATION; OLIGOPEPTIDES; STEREOISOMERISM; TRYPTOPHAN;

EID: 0037635962     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10232     Document Type: Article

References (22)

1. Wulff G, Sarhan A. The use of polymers with enzyme-analogous structures for the recognition of racemates. Angew Chem Int Ed Engl 1972; 11:341.
2. Shea KJ. Molecular imprinting of synthetic network polymers. Trends Polym Sci 1994;2:166-173.
3. Takeuchi T, Matsui J. Molecular imprinting: an approach to "tailor-made" synthetic polymers with biomimetic functions. Acta Polymer 1996;47:471-480.
4. Wulff G. Fitting molecules into polymeric receptors. CHEMTECH 1998;November:19-26.
5. Piletsky SA, Panasyuk TL, Piletskaya EV, Nicholls IA, Ulbricht M. Receptor and transport properties of imprinted polymer membranes - a review. J Membr Sci 1999;157:263-278.
6. Haupt K, Mosbach K. Molecularly imprinted polymers and their use in biomimetic sensors. Chem Rev 2000;100:2495-2504.
7. Yoshikawa M. Molecularly imprinted polymeric membranes for optical resolution. In: Bartsch RA; Maeda M, editors. Molecular and ionic recognition with imprinted polymers (ACS Symposium Series 703). Washington, DC: American Chemical Society; 1998, Chap. 12.
8. Yoshikawa M, Izumi J, Kitao T, Sakamoto S. Molecularly imprinted polymeric membranes containing DIDE derivatives for optical resolution of amino acids. Macromolecules 1996;29:8197-8203.
9. Yoshikawa M, Ooi T, Izumi J. Alternative molecularly imprinted membranes from a derivative of natural polymer, cellulose acetate. J Appl Polym Sci 1999;72:493-499.
10. Kondo Y, Yoshikawa M, Okushita H. Molecularly imprinted polyamide membranes for chiral recognition. Polym Bull 2000;44:517-524.
11. Riddick JA, Bunger WB, Sakano TK. Organic solvents, 4th ed. New York: John Wiley & Sons; 1986.
12. Perrin DP, Armarego WLF. Purification of laboratory chemicals 3rd ed. Oxford: Pergamon Press; 1988.
13. Merrifield RB. Solid phase synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 1963;85:2149-2154.
14. Merrifield RB, Vizioli LD, Boman HG. Synthesis of the antibacterial peptide cecropin A(1-33). Biochemistry 1982;21:5020-5031.
15. Merrifield RB. Solid phase synthesis. Angew Chem Int Ed Engl 1985; 24:799-810.
16. Yamashiro D, Li CH. Synthesis of a pentekontapeptide with high lipolytic activity corresponding to the carboxyl-terminal fifty amino acids of ovine β-lipotropin. Proc Natl Acad Sci USA 1974;71:4945-4949.
17. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of prptides. Anal Biochem 1970;34:595-598.
18. Knecht R, Chang J-Y. Liquid chromatographic determination of amino acids after gas-phase hydrolysis and derivatization with (dimethylamino)azobenzenesulfonyl chloride. Anal Chem 1986;58:2375-2379.
19. Yoshikawa M, Izumi J, Kitao T. Alternative molecular imprinting, a facile way to introduce chiral recognition sites. React Funct Polym 1999;42:93-102.
20. Yoshikawa M, Izumi J, Kitao T. Enantioselective electrodialysis of amino acids with charged polar side chains through molecularly imprinted polymeric membranes containing DIDE derivatives. Polym J 1997;29:205-210.
21. Yoshikawa M, Fujisawa T, Izumi J, Kitao T, Sakamoto S. Chiral recognition of N-α-acetyltryptophans with molecularly imprinted polymeric membranes containing DVNE derivatives. Sen'i Gakkaishi 1998;54:77-84.
22. Yoshikawa M, Fujisawa T, Izumi J, Kitao T, Sakamoto S. Molecularly imprinted polymeric membranes involving tetrapeptide EQKL derivatives as chiral recognition sites toward amino acids. Anal Chim Acta 1998;365:59-67.