Narzędzia chemii kombinatorycznej : nośniki stosowane w syntezie organicznej związków nisko- i wysokocząsteczkowych

• Autorzy: Łaźny R. , Nodzewska A.

Warianty tytułu

EN

Tools for combinatorial chemistry: supports used for organic synthesis of small molecules and macromolecules

• Języki publikacji: PL

Abstrakty

EN

Progress in combinatorial chemistry is largely determined by development of specific synthetic organic chemistry tools such as solid supports, linkers, polymer supported reactions and methods of analysis, screening and deconvolution of combinatorial libraries. This review article presents basic terms related to polymer supported synthesis, enumerates major advantages of supported reactions, and gives a comprehensive, up to date, overview of support matrices used for immobilization of small and large molecules. The review covers the literature up to September 2002. The supports reviewed include (i) polymeric gels (Merrifield gel, TentaGel, ArgoGelTM, JandaJelTM, PEGA, PEG-PS, PEG-POP, SPOCC, PS-TTEGDA, CLEAR, DendroGel, Pepsyn, and Sucholeiki paramagnetic gel), (ii) soluble polymers (LPS, PEG, ROMP-polymer, PAMAM-dendrymer, Boltron), (iii) macroporous supports (CPG, Pepsyn K, PolyHIPE, ArgoPoreTM) and other developments including SMART reactors, MicroTubeTM, membranes, pins, and cellulose. For most of the supports reviewed basic characteristics such as swelling in different solvents, solvent usability, typical loading, typical anchoring groups, preparation, and recent applications are given or cited. The reviewed literature suggests that the supports most often used for synthesis of small molecules and peptides are based on gel matrices. The variety of available supports, many of which were introduced in the last years, shows that this area of synthetic methodology may grow dynamically in the future.

Słowa kluczowe

PL

chemia kombinatoryczna; nośnik polimeryczny; synteza na nośniku

EN

combinatorial chemistry; polymer supported; organic synthesis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2003
• Tom: [Z] 57, 7-8
• Strony: 587--625
• Opis fizyczny: Bibliogr. 72 poz., schem., tab., wykr.

Twórcy

autor

Łaźny R.

• Uniwersytet w Białymstoku, Instytut Chemii, Al. Piłsudskiego 11/4, 15-443 Białystok

autor

Nodzewska A.

• Uniwersytet w Białymstoku, Instytut Chemii, Al. Piłsudskiego 11/4, 15-443 Białystok

Bibliografia

• [1] W Lewgowd, A. Stańczak, Farmacja Polska, 2001, 57, 11.
• [2] I.Z. Siemion, Wiad. Chem., 1998, 52, 311.
• [3] A. Furka, F. Sebestyen, G. Dibo, I4th. Int Conger. Blochem: Prague 1988, 5, 47, Abstr 10th Symp. Med. Chem., Budapest, 1988, 288.
• [4] R.A. Houghten, C. Pinilla, S.E. Blondelle, J.R. Appel, C.T. Dooley, J.H. Cuervo, Nature, 1991, 354, 84.
• [5] G.P. Smith, V.A. Petrenko Chem Rev., 1997, 97, 391.
• [6] FM. Menger, J. Ding, V. Barragan, J. Org. Chem., 1998, 63, 7578.
• [7] A.M. Porte, J. Reibcnspies, K. Burgess, J. Am. Chem. Soc., 1998, 120, 9180.
• [8] S. Dahmen, S. Brase, Synthesis, 2001, 10, 1431.
• [9] S. Brase, S. Dahmen, F. Lauterwasser, N.E. Leadbeater, E.L. Sharp, Bioorg. Med. Chem. Lett., 2002, 12, 1849.
• [10] M.D. Weingarten, K. Sekanina, W.C. Still, J. Am. Chem. Soc., 1998, 120, 9112.
• [11] R.B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
• [12] R.L. Letsinger, M.J. Komet, J. Am. Chem. Soc., 1963, 85, 3045.
• [13] S.R. Wilson, A.W. Czarnik, Combinatorial chemistry. Synthesis and Application, Eds, Wiley & Sons New York, 1997, 1.
• [14] I.W. James, Tetrahedron, 1999, 55, 4855.
• [15] F. Guillier, D. Orain, M. Bradley, Chem. Rev., 2000, 100, 2091.
• [16] S. Brase, S. Dahmen, Linker for Solid-phase Synthesis [w:] Handbook of Combinatorial Chemistry. K.C. Nicolaou Ed., Wiley-VCH, New York, 2002.
• [17] D. Maclean, J.J. Baldwin, V.T. Ivanov, Y. Kato, A. Shaw, P. Schneider, E.M Gordon, Pure Appl. Chem., 1999, 71, 2349.
• [18] P. Seneci, Solid-Phase Synthesis and Combinatorial Technologies. John Wiley and Sons, New York, 2000.
• [19] D.J. Gravert, K.D. Janda, Chem. Rev., 1997, 97, 489.
• [20] A. Basso, B. Evans, N. Pegg, M. Bradley, Tetrahedron Lett., 2000, 41, 3763.
• [21] Katalog firmy NovaBiochem, 2000.
• [22] D.C Sherrington, J. Chem. Soc. Chem. Commun., 1998, 2275.
• [23] P. Hodge, Chem. Soc. Rev., 1997, 26, 417.
• [24] Katalog firmy Polymer Laboratories, 2000.
• [25] J. Skarżewski, Wprowadzenie do syntezy organicznej, Wydawnictwo Naukowe PWN, Warszawa, 1999.
• [26] Katalog firmy Fluka 2001/2002.
• [27] Informacja Techniczna firmy Argonaut Technologies.
• [28] E.E Swayze, Tetrahedron Lett., 1997, 38, 8643.
• [29] P.H. Toy, K.D. Janda, Tetrahedron Lett., 1999, 40, 6329.
• [30] P.H. Toy, T.S. Reger, K.D. Janda, Aldrichimica Acta., 2000, 33, No. 3, 87.
• [31] P. Giribay, P.H. Toy, T. Hoeg-Jensen, K.D. Janda, Synlett, 1999, 1438.
• [32] J.A. Moss, T.J. Dickerson, K.D. Janda, Tetrahedron Lett., 2002, 43, 37.
• [33] M. Meldal, Tetrahedron Lett., 1992, 33, 3077.
• [34] J. Rademann, M. Grotli, M. Meldal, K. Bock, J. Am. Chem. Soc., 1999, 121, 5459.
• [35] M. Winter, R. Warrass, Resins and anchors for solid phase organic synthesis [w:] Combinatorial Chemistry. A practical approach. H. Fenniri Ed., Oxford University Press, Warsaw 2000.
• [36] M. Renil, M. Meldal, Tetrahedron Lett., 1996, 37, 6185.
• [37] J. Buchardt, M. Meldal, Tetrahedron Lett., 1998, 39, 8695.
• [38] K.S. Kumar, P. Rajsekharan, Tetrahedron, 1999, 10437.
• [39] J.M. Steward, J.D. Young, [w:] Solid Phase Peptide Synthesis; 2nd cd., Pierce Chemical Co.; Rockford, IL, 1984, 54.
• [40] M. Kempe, F. Barany, J. Am. Chem. Soc., 1996, 118, 7083.
• [41] S. Lebreton, N. Newcombe, M. Bradley, Tetrahedron Lett., 2002, 43, 2475.
• [42] A. Basso, N. Pegg, B. Evans, M. Bradley, Eur. J. Org. Chem., 2000, 3887.
• [43] S. Lebreton, N. Newcombe, M. Bradley, Tetrahedron Lett., 2002, 43, 2479.
• [44] A. Mahajan, S.R. Chhabra, W.C. Chan, Tetrahedron Lett., 1999, 40, 4909.
• [45] R. Haag, Chem. Eur. J., 2001, 7, 327.
• [46] E. Atherton, E. Brown, R.C. Shepparg, J. Chem. Soc. Chem. Commun., 1981, 1151.
• [47] R. Arshady, E. Atherton, M.J. Gait, K. Lee, R.C. Sheppard, J. Chem. Soc. Chem. Comm., 1979, 423.
• [48] I. Sucholeiki, J.M. Perez, Tetrahedron Lett., 1999, 40, 3531.
• [49] I. Sucholeiki, J.M. Perez, P.D. Owens, Tetrahedron Lett., 2001, 42, 3279.
• [50] P.H. Toy, K.D. Janda, Acc. Chem. Res., 2000, 33, 546.
• [51] P. Wentworth, Jr. K.D. Janda, J. Chem. Soc. Chem. Commun., 1991, 1917.
• [52] A.G.M. Barrett, S.M. Cramp, R.S. Roberts, Org. Lett., 1999, 1, 1083.
• [53] R.M. Kim, M. Manna, S.M. Hutchins, P.R. Griffin, N.A. Yates, Proc. Natl. Acad. Sci. U.S.A., 1996, 93, 10012.
• [54] D.A. Tomalia, Macromolecules, 1986, 19, 2466.
• [55] C.J. Hawker, J.M.J. Frechet, J. Am. Chem. Soc., 1990, 112, 7638.
• [56] S. Lebreton, M. Monaghan, M. Bradley, Aldrichimica Acta, 2001, 34, 75.
• [57] A.B. Kantchev, J.R. Parquette, Tetrahedron Lett., 1999, 40, 8049.
• [58] P.W. Small, D.C. Sherrington, J. Chem. Soc. Chem. Commun., 1989, 1589.
• [59] H. Deleuze, B. Maillard, O. Mondain-Monval, Bioorg. Med. Chem. Lett., 2002, 12, 1877.
• [60] Informacja Techniczna firmy Argonaut Technologies.
• [61] M.D. Matteucci, M.H. Caruthers, J. Am. Chem. Soc., 1981, 103, 3185.
• [62] J.F.W. Keana, M. Shimuzu, K.K. Jemstedt, J. Org. Chem., 1986, 51, 1641.
• [63] Informacja Techniczna firmy Silicycle, http://www.silicycle.com
• [64] S.B. Daniels, M.S. Bematowicz, J.M. Coull, H. Koster, Tetrahedron Lett., 1989, 30, 4345.
• [65] N. Hird, I. Hughes, D. Hunter, M.G.J.T. Morrison, D.C. Sherrington, L. Stevenson, Tetrahedron, 1999, 55, 9575.
• [66] R. Li, X.-Y. Xiao, A.W. Czamik, Tetrahedron Lett., 1998, 39, 8581.
• [67] T. Takasashi, S. Ebata, T. Doi, Tetrahedron Lett., 1998, 39, 1369.
• [68] E.J. Moran, S. Sarshar, J.F. Cargill, M.M. Shahbaz, A. Lio, A.M.M. Mjalli, R.W. Armstrong, J. Am. Chem. Soc., 1995, 117, 10787.
• [69] K.C. Nicolaou, X.-Y. Xiao, Z. Parandoosh, A. Seneyei, M.P. Nova, Angew. Chem. Int. Ed. Engl., 1995, 34, 2289.
• [70] R.H. Berg, K. Almdal, W.B. Pedersen, A. Holm, J.P. Tam, R.B. Merrifield, J. Am. Chem. Soc., 1989, 111, 8024.
• [71] R-V. Devivar, S.L. Koontz, W.J. Peltier, J.E. Pearson, T.A. Guillory, J.D. Fabricant, Bioorg. Med. Chem. Lett., 1999, 9, 1239.
• [72] R. Frank, R. Doring, Tetrahedron, 1988, 44, 6031.

Uwagi

PL

Opracowane ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023)