Template-mediated synthesis of a polymeric receptor specific to amino acid sequences

Angewandte Chemie - International Edition

Volumn 38, Issue 13-14, 1999, Pages 2057-2060

  Klein, Jens U ^a   Whitcombe, Michael J ^a   Mulholland, Francis ^a   Vulfson, Evgeny N ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Imprinting; Molecular recognition; Peptides; Polymers; Receptors

Indexed keywords

PEPTIDE; POLYMER; RECEPTOR;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; MOLECULAR RECOGNITION; PEPTIDE ANALYSIS; PROTEIN BINDING; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033549571     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990712)38:13/14<2057::aid-anie2057>3.0.co;2-g     Document Type: Article

References (25)

1. L. Pauling, J. Am. Chem. Soc. 1940, 62, 2643-2657.
2. Reviews: a) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; G. Wulff, Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
3. Reviews: a) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; G. Wulff, Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
4. b) K. J. Shea, Trends Polym. Sci. 1998, 2, 166-173;
5. c) K. Mosbach, O. Ramström, Bio/Technology 1996, 14, 163-170;
6. d) E. N. Vulfson, C. Alexander, M. J. Whitcombe, Chem. Br. 1997, 33, 23-26. For a notable recent report on the use of combinatorial methods in molecular imprinting, see
7. e) T. Takeuchi, D. Fukuma, J. Matsui, Anal. Chem. 1999, 71, 285-290.
8. G. Vlatakis, L. I. Andersson, R. Müller, K. Mosbach, Nature 1993, 361, 645-647.
9. O. Ramström, L. Ye, K. Mosbach, Chem. Biol. 1996, 3, 471-477.
10. M. J. Whitcombe, M. E. Rodriguez, P. Villar, E. N. Vulfson, J. Am. Chem. Soc. 1995, 117, 7105-7111.
11. Amino acid derivatives and short peptides have been noncovalently imprinted in a number of studies that have produced polymers capable of optical resolution. See for example a) B. Sellergren, M. Lepistö, K. Mosbach, J. Am. Chem. Soc. 1988, 110, 5853-5860;
12. b) I. A. Nicholls, L. I. Andersson, K. Mosbach, B. Ekberg, Trends Biotechnol. 1995, 13, 47-51;
13. c) C. Yu, K. Mosbach, J. Org. Chem. 1997, 62, 4057-4064;
14. d) S. Vidyasankar, M. Ru, F. H. Arnold, J. Chromatogr. A 1997, 775, 51-63;
15. e) J. M. Lin, T. Nakagama, K. Uchiyama, T. Hobo, J. Pharm. Biomed. Anal. 1997, 15, 1351-1358;
16. f) O. Ramström, I. A. Nicholls, K. Mosbach, Tetrahedron: Asymmetry. 1994, 5, 649-656;
17. g) M. Kempe, K. Mosbach, Tetrahedron Lett. 1995, 36, 3563-3566;
18. h) L. I. Andersson, R. Müller, G. Vlatakis, K. Mosbach, Proc. Natl. Acad. Sci. USA 1995, 92, 4788-4792.
19. M. Lübke, M. J. Whitcombe, E. N. Vulfson, J. Am. Chem. Soc. 1998, 120, 13 342-13 348.
20. Covalent imprinting with polymerizable carboxylic esters (without spacers) has been successfully carried out before, see B. Sellergren, L. Andersson, J. Org. Chem. 1990, 55, 3381-3383.
21. This monomer has previously been used in combination with methacrylic acid to imprint amino acid derivatives, see O. Ramström, L. I. Andersson, K. Mosbach, J. Org. Chem. 1993, 58, 7562-7564.
22. 1H NMR studies on a model compound, N-(4-hexadecylphenyl)-2-methacryloyloxybenzamide, confirmed the presence of an intramolecular hydrogen bond between the amide N proton and the adjacent oxygen atom.
23. X. C. Liu, K. Mosbach, Macromol. Rapid Commun. 1998, 19, 671-674.
24. Selectivity between aspartic and glutamic acid derivatives has previously been reported for imprinted polymers based on methacrylic acid, see L. I. Andersson, K. Mosbach, J. Chromatogr. Sci. 1990, 516, 313-322.
25. G. H. Chen, Z. B. Guan, C. T. Chen, L. T. Fu, V Sundaresan, F. H. Arnold, Nat. Biotechnol. 1997, 15, 354-357.