Amino-derivatised beaded cellulose gels. Novel accessible and biodegradable scavenger resins for solution phase combinatorial synthesis

Green Chemistry

Volumn 2, Issue 2, 2000, Pages 57-62

  Chesney, Antony ^a,c   Barnwell, Philip ^a   Stonehouse, David F ^a,b   Steel, Patrick G ^b  

^a Civil and Geotechnical Laboratory   (United Kingdom)

^b DURHAM UNIVERSITY   (United Kingdom)

^c JOHNSON MATTHEY CATALYSTS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044520583     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909655h     Document Type: Article

References (40)

1. For general reviews of combinatorial chemistry, see: F. Balkenhohl, C. von dem Bussche-Huennefeld, A. Lansky and C. Zechel, Angew. Chem., Int. Ed. Engl., 1996, 35, 2288;
2. L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555;
3. E. M. Gordon, M. A. Gallop and D. V. Patel, Acc. Chem. Res., 1996, 29, 144;
4. J. C. Hogan Jr, Nat. Biotechnol., 1997, 15, 328.
5. For an overview of analytical techniques employed in combinatorial synthesis, see: B. A. Bunin, The Combinatorial Index, Academic Press, New York, 1998;
6. Combinatorial Chemistry: Synthesis, Analysis, Screening, ed. G. Yung, Wiley-VCH, Weinheim, 1999.
7. For reviews of methods employed to affect solution-phase combinatorial chemistry, see: R. Storer, Drug. Discov. Today, 1996, 1, 248;
8. A. Chuckolowski, T. Masquelin, D. Obrecht, J. Stadlweiser and J. M. Villagordo, Chimica, 1996, 50, 525;
9. D. M. Coe and R. Storer, Annu. Rep. Comb. Chem. Mol. Diversity, 1997, 1, 50;
10. A. T. Merritt, Comb. Chem. High Throughput Screening, 1998, 1, 57.
11. B. Cornilis, Angew. Chem., Int. Ed. Engl., 1997, 36, 2057;
12. D. P. Curran and S. Hadida, J. Am. Chem. Soc., 1996, 118, 2531;
13. D. P. Curran and M. Hoshino, J. Org. Chem., 1996, 61, 6480;
14. A. Struder and D. P. Curran, Tetrahedron, 1997, 53, 6681.
15. M. G. Siegel, P. J. Hahn, B. A. Dressman, J. E. Fritz, J. R. Grunwell and S. W. Kaldor, Tetrahedron Lett., 1997, 38, 3357;
16. L. M. Gayo and M. J. Suto, Tetrahedron Lett., 1997, 38, 516;
17. R. M. Lawrence, S. A. Biller, O. M. Fryszman and M. A. Poss, Synthesis, 1997, 553;
18. B. A. Kukarni and A. Ganesan, Angew. Chem., Int. Ed. Engl., 1997, 36, 2454.
19. D. J. Gravert and K. D. Janda, Chem. Rev., 1997, 97, 489;
20. D. J. Gravert and K. D. Kanda, Drugs Fut., 1997, 22, 1147.
21. For reviews on the applications of scavenger resins, see: (a) D. L. Flynn, R. V. Devraj and J. J. Parlow, Curr. Opin. Drug. Discov. Dev., 1998, 1, 41;
22. (b) J. J. Parlow, R. V. Devraj and M. S. South., Curr. Opin. Chem. Biol., 1999, 3, 320.
23. For a discussion on renewable sources of cellulose materials for ion-exchange purposes, see: I. Bartle and N. Oliver, Green Chem., 1998, 1, G6.
24. D. Klemm, B. Philipp, T. Heinze, U. Heinze and W. Wagenknecht, Comprehensive Cellulose Chemistry, Wiley-VCH, Chichester, 1998, vol. 2.
25. For examples, see: (a) S. C. Burton, N. W. Haggarty and D. R. K. Harding, Biotechnol. Bioeng., 1997, 56, 45;
26. (b) S. C. Burton and D. R. K. Harding, J. Chromatogr. A, 1997, 775, 29;
27. (c) S. C. Burton and D. R. K. Harding, J. Chromatogr. A, 1997, 775, 273.
28. The actual structure of 6 may not truly be that depicted, and will in fact be a complex number of structures depending on the degree of crosslinking which the tris(2-aminoethyl)amine has performed on epoxide 4.
29. It should be noted that 10 ml of resin 6 in its aqueous-solvated form has a dry mass of ca. 1 g, as determined by residual mass measurements after oven drying at elevated temperatures for 16 h.
30. Information taken from the Argonaut Technologies Inc (San Fransisco , CA) 1998 catalogue and technical data sheets.
31. A. Chesney, P. G. Steel and D. F. Stonehouse, J. Comb. Chem., submitted.
32. R. G. H. Siu, The Microbial Decomposition of Cellulose, Reinhold, New York, 1951;
33. The Biosynthesis and Biodegradation of Cellulose, ed. C. H. Haigler and P. J. Weimer, Dekker, New York, 1991.
34. For a review of the conversion of cellulose directly into ethanol by a fermentation process, see: P. Chandrakat and V. S. Bisaria, Crit. Rev. Biotechnol., 1998, 18, 295.
35. Patents granted to B. Hartley and B. S. Hartley, Elsworth Biotechnology Ltd; WO 8809379 A, 1988, EP 370023 B, 1990 and US 5182199 A, 1993.
36. V. Richert and A. Zimmer, Genetic. Eng. News, 1998, Oct. 1, p. 21.
37. For a discussion on recent advances in the degradation of non-soluble cellulose materials by enzymes, see: B. Saake, S. Horner and J. Puls, in Cellulose Derivatives; Modification, Characterisation and Nanostructures, ed. T. H. Heinze and W. G. Glasser, ACS Symp. Ser. 688, American Chemical Society, Washington, DC, 1998, ch. 15.
38. For the application of the hexokinase assay in glucose determination, see: R. J. L. Bondar and D. C. Mead, Clin. Chem., 1974, 20, 586;
39. A. Kunsst, B. Draeger and J. Ziegenhorn, in Methods of Enzymatic Analysis, ed. H. U. Bergmeyer, Academic Press, New York, 1984, vol. 2, p. 163.
40. The glucose (HK) assay kit is commercially available from Sigma-Aldrich.