Tagging molecules with linear polymers: Biocatalytic transformation of substrates anchored on soluble macromolecules

Combinatorial Chemistry and High Throughput Screening

Volumn 13, Issue 1, 2010, Pages 45-53

  Cornaggia, Claudio ^a   Pasini, Dario ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

Biocatalysis; Combinatorial synthesis; High throughput synthesis; Linear polymers; Macromolecules; Organic chemistry; Organic tags; Solution phase synthesis

Indexed keywords

4 BENZYLOXY 2 BUTANOL; ACETONITRILE; AGAROSE; ALCOHOL DERIVATIVE; BUTANOL; FLUOROCARBON; FUNGAL ENZYME; LIPASE B; MACROGOL; PENICILLIN AMIDASE; POLYSTYRENE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CANDIDA ANTARCTICA; CANDIDA RUGOSA; CHEMICAL LABELING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; HYDROLYSIS; MACROMOLECULE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; TRANSESTERIFICATION;

BIOCATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; POLYMERS; SOLUBILITY;

EID: 77949789092     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620710790218177     Document Type: Article

References (55)

1. Faber, K. Biotransformations in Organic Chemistry; Springer: Berlin, 2000.
2. Rothenberg, G. Catalysis: Concepts and Green Applications, Wiley-VCH: Weinheim, 2008.
3. Sheldon, R.A.E factors, green chemistry and catalysis: an odyssey. Chem. Commun., 2008, 3352-3365.
4. Sheldon, R.A. Enzyme immobilization: The quest for optimum performance. Adv. Synth. Catal., 2007, 349, 1289-1307.
5. Merrifield, R.B. Solid phase synthesis. Angew. Chem. Int. Ed. Engl., 1985, 24, 799-810 (Nobel Lecture).
6. For a recent example about "mix and split" library generation, see: Simon, R.A.; Schuresko, L.; Dendukuri, N.; Goers, E.; Murphy, B.; Lokey, R.S. One-bead-one-compound library of end-capped dipeptides and deconvolution by microflow NMR. J. Comb. Chem., 2005, 7, 697-702.
7. For general references, see: Seneci, P. Solid Phase and Combinatorial Technologies, Wiley, New York, 2000.
8. Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M. Applications of Combinatorial Technologies to Drug Discovery. 1. Background and Peptide Combinatorial Libraries. J. Med. Chem., 1994, 37, 1233-1251.
9. Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J. Med. Chem., 1994, 37, 1385-1401.
10. Toy, P.H.; Janda, K.D. Soluble polymer-supported organic synthesis. Acc. Chem. Res., 2000, 33, 546-554.
11. Osburn, P.L.; Bergbreiter, D.E. Molecular engineering of organic reagents and catalysts using soluble polymers. Progr. Polym. Sci., 2001, 26, 2015-2081.
12. Clapham, B.; Reger, T.S.; Janda, K.D. Polymer-supported catalysis in synthetic organic chemistry. Tetrahedron, 2001, 57, 4637-4662.
13. Dickerson, T.J.; Reed, N.N.; Janda, K.D. Soluble polymers as scaffolds for recoverable catalysts and reagents. Chem. Rev., 2002, 102, 3325-3344.
14. Bergbreiter, D.E. Using soluble polymers to recover catalysts and ligands. Chem. Rev., 2002, 102, 3345-3384.
15. Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-supported organic catalysts. Chem. Rev., 2003, 103, 3401-3429.
16. Bergbreiter, D.E.; Sung, S.D. Liquid/liquid biphasic recovery/reuse of soluble polymier-supported catalysts. Adv. Synth. Catal., 2006, 348, 1352-1366.
17. Gravert, D.J.; Janda, K.D. Organic synthesis on soluble polymer supports: Liquid-phase methodologies. Chem. Rev., 1997, 97, 489-509.
18. Wenthworth, P. Jr.; Janda, K.D. Liquid-phase chemistry: recent advances in soluble polymer-supported catalysts, reagents and synthesis. Chem. Commun., 1999, 1917-1924.
19. Kollhofer, A.; Plenio, H. Homogeneous catalysts supported on soluble polymers: biphasic sonogashira coupling of aryl halides and acetylenes using MeOPEG-bound phosphine-palladium catalysts for efficient catalyst recycling. Chem. Eur. J., 2003, 9, 1416-1425.
20. Benaglia, M.; Guizzetti, S.; Rigamonti, C.; Puglisi, A. PEG-supported pyridylthioesters for racemization-free amide synthesis: a reagent that allows simultaneous product formation and removal from the polymer. Tetrahedron, 2005, 61, 12100-12106.
21. McNamara, C.; Dixon, M.J.; Bradley, M. Recoverable catalysts and reagents using recyclable polystyrene-based supports. Chem. Rev., 2002, 102, 3275-3300.
22. Zheng, X.; Jones, C. W.; Weck, M. Poly(styrene)-supported cosalen complexes as efficient recyclable catalysts for the hydrolytic kinetic resolution of epichlorohydrin. Chem. Eur. J., 2006, 12, 576-583.
23. Bergbreiter, D. E.; Li, C. Poly(4-tert-butylstyrene) as a soluble polymer support in homogeneous catalysis. Org. Lett., 2003, 5, 2445-2447.
24. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. A soluble polymer-bound Evans' chiral auxiliary: synthesis, characterization and use in cycloaddition reactions. Tetrahedron: Asymmetry, 2002, 13, 333-337.
25. Lakshmipathi, P.; Crevisy, C.; Gree, R. Reaction monitoring in LPOS by F-19 NMR. Study of soluble polymer supports with fluorine in spacer or linker components of supports. J. Comb. Chem., 2002, 4, 612-621.
26. For a recent review on the use of dendrimers in homogeneous catalysis, see: Helms, B.; Fréchet, J.M.J. The dendrimer effect in homogeneous catalysis. Adv. Synth. Catal., 2006, 348, 1125-1148.
27. Ams, M.R.; Wilcox, C.S. Benzil-tethered precipitons for controlling solubility: A round-trip energy-transfer mechanism in the isomerization of extended stilbene analogues. J. Am. Chem. Soc., 2007, 129, 3966-3972.
28. Safety-catch linkers are a particularly sophisticated form of attachment, whereby a linker present throughout the library assembly in a relatively inert form is activated and made labile at the end of the synthesis to release the products from resins: see, for example: Backes, B.J.; Virgilio, A.A.; Ellman, J.A. Activation method to prepare a highly reactive acylsulfonamide "safety-catch" linker for solid-phase synthesis. J. Am. Chem. Soc., 1996, 118, 3055-3056.
29. Todd, M.H.; Oliver, S.F.; Abell, C. A novel safety-catch linker for the solid-phase synthesis of amides and esters. Org. Lett., 1999, 1, 1149-1151.
30. Grether, U.; Waldmann, H. An enzyme-labile safety catch linker for synthesis on a soluble polymeric support. Chem. Eur. J., 2001, 7, 959-971.
31. Reents, R.; Jeyaraj, D.; Waldmann, H. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M.R.; Ed.; Wiley-VCH: Weinheim, 2003, pp. 445-466.
32. Nogawa, M.; Shimojo, M.; Matsumoto, K.; Okudomi, M.; Nemoto, Y.; Ohta, H. inetic resolution of poly(ethylene glycol)-supported carbonates by enzymatic hydrolysis. Tetrahedron, 2006, 62, 7300-7306.
33. Okudomi, M.; Shimojo, M.; Nogawa, M.; Hamanaka, A.; Taketa, N.; Matsumoto, T. Easy separation of optically active products by enzymatic hydrolysis of soluble polymer-supported substrates. Tetrahedron Lett., 2007, 48, 8540-8543.
34. For leading references about controlled or "living" free radical polymerization, see: Matyjaszewski, K.; Xia, J. Atom transfer radical polymerization. Chem. Rev., 2001, 101, 2921-2990.
35. Hawker, C.J.; Bosman, A. W.; Harth, E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem. Rev., 2001, 101, 3661-3688.
36. Moad, G.; Rizzardo, E.; Thang, S.H. Living radical polymerization by the RAFT process - A first update. Aust. J. Chem., 2006, 59, 669-692.
37. Barner-Kowollik, C.; Perrier, S. The future of reversible addition fragmentation chain transfer polymerization. J. Polym. Sci, A, 2008, 46, 5715-5723.
38. Pasini, D.; Filippini, M.; Pianetti, I.; Pregnolato, M. Efficient biocatalytic cleavage and recovery of organic substrates supported on soluble polymers. Adv. Synth. Catal., 2007, 349, 971-978.
39. Padovani, M.; Hilker, I.; Duxbury, C. J.; Heise, A. Functionalization of polymers with high precision by dual regio-and stereoselective enzymatic reactions. Macromolecules, 2008, 41, 2439-2444.
40. Kawabata, N. Syntheses of biodegradable vinyl polymers by insertion of N-benzyl-4-vinylpyridinium chloride into the main chain. React. Funct. Polym., 2007, 67, 1292-1300
41. Horváth T.; Rábai J. Facile catalyst separation without water - fluorous biphase hydroformilations of olefins. Science, 1994, 266, 72-75.
42. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.Y.; Jeger, P.; Wipf, P.; Curran, D.P. Fluorous synthesis: a fluorous-phase strategy for improving separation efficiency in organic synthesis. Science, 1997, 275, 823-826.
43. Swaleh, S.M.; Hungerhoff, B.; Sonnenschein, H.; Theil, F. Separation of enantiomers by lipase-catalyzed fluorous-phase delabeling. Tetrahedron, 2002, 58, 4085-4089.
44. Hungerhoff, B.; Sonnenschein, H.; Theil, F. Separation of enantiomers by extraction based on lipase-catalyzed enantiomer-selective fluorous-phase labeling. Angew. Chem. Int. Ed., 2001, 40, 2492-2494.
45. Hungerhoff B.; Sonnenschein H.; Theil F. Combining lipase-catalyzed enantiomer-selective acylation with fluorous phase labeling: A new method for the resolution of racemic alcohols. J. Org. Chem., 2002, 67, 1781-1785.
46. Luo, Z.; Swaleh, M.S.; Theil, F.; Curran, D.P. Resolution of 1-(2-naphthyl)ethanol by a combination of an enzyme-catalyzed kinetic resolution with a fluorous triphasic separative reaction. Org. Lett., 2002, 4, 2585-2587.
47. Nakamura, H.; Linclau, B.; Curran, D.P. Fluorous triphasic reactions: transportative deprotection of fluorous silyl ethers with concomitant purification. J. Am. Chem. Soc., 2001, 123, 10119-10120.
48. Beier P.; O'Hagan D. Enantiomeric partitioning using fluorous biphase methodology for lipase-mediated (trans)esterifications. Chem. Commun., 2002, 1680-1681.
49. Tavener, S.J.; Clark, J.H. Can fluorine chemistry be green chemistry? J. Fluorine Chem., 2003, 123, 31-36.
50. Ellis, D. A.; Moody, C. A.; Mabury, S. A. In Organofluorines; Neilson, A. H., Ed.; Springer-Verlag: Berlin, 2002.
51. Chu, Q.; Henry, C.; Curran, D.P. Second-generation tags for fluorous chemistry exemplified with a new fluorous mitsunobu reagent. Org. Lett., 2008, 10, 2453-2456.
52. Lutz, J.-F.; Andrieu, J.; Üzgün, S.; Rudolph, C.; Agarwal, S. Biocompatible, thermoresponsive, and biodegradable: Simple preparation of "all-in-one" biorelevant polymers. Macromolecules, 2007, 40, 8540-8543.
53. Schild, H.G. Poly(N-isopropylacrylamide)-experiment, theory and application. Prog. Polym. Sci., 1992, 17, 163-249.
54. Huang, X.F.; Witte, K.L.; Bergbreiter, D.E.; Wong, C.H. Homogenous enzymatic synthesis using a thermo-responsive water-soluble polymer support. Adv. Synth. Catal., 2001, 343, 675-681.
55. Kim, S.; Tsuruyama, A.; Ohmori, A.; Chiba, K. Solution-phase oligosaccharide synthesis in a cycloalkane-based thermomorphic system. Chem. Commun., 2008, 1816-1818 and references therein.