Abstract
One major challenge in combinatorial chemistry is to find biologically relevant starting points in the chemical universe around which compound libraries should be produced. Natural products represent such biologically validated starting points. Progress in Solid-Phase Organic Synthesis (SPOS) has enabled now the combination of natural product synthesis with combinatorial methods. Two strategies can be distinguished:(1) Attachment of a natural product core structure onto solid phase and subsequent modification of functional groups, or (2) total synthesis of the complete natural product scaffold on solid phase. A complementary approach identifies privileged structures among natural product scaffolds, which serve as inspiration for library synthesis. In this review the current status and the challenges of combinatorial natural product synthesis on solid phase are presented.
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References
Mitchison TJ (1994) Chem Biol 1:3
Schreiber SL (1998) Biorg Med Chem 6:1127
Alaimo PJ, Shogren-Knaak MA, Shokat KM (2001) Curr Opin Chem Biol 5:60
Service RF (1999) Science 285:184
Breinbauer R, Vetter IR, Waldmann H (2002) Angew Chem Int Ed 41:2879
Roth HJ (2005) Curr Opin Chem Biol 9:293
Fergus S, Bender A, Spring DR (2005) Curr Opin Chem Biol 9:304
Selzer P, Roth HJ, Ertl P, Schuffenhauer A (2005) Curr Opin Chem Biol 9:310
Ajay, Walters WP, Murcko MA (1998) J Med Chem 41:3314
Keller TH, Pichota A, Yin Z (2006) Curr Opin Chem Biol 10:357
Dominik A (2006) In: Bannwarth W, Hinzen B (eds) Combinatorial Chemistry. Wiley, Weinheim, pp 559–613
Pernerstorfer J (2002) In: Nicolaou KC, Hanko R, Hartwig W (eds) Handbook of Combinatorial Chemistry. Wiley, Weinheim, pp 725–742
Bohacek RS, McMartin C, Guida WC (1996) Med Res Rev 16:3
Schreiber SL (2000) Science 287:1964
Burke MD, Berger EM, Schreiber SL (2003) Science 302:613
Burke MD, Schreiber SL (2004) Angew Chem Int Ed 43:46
Rishton GM (1997) Drug Discov Today 2:382
Golebiowski A, Klopfenstein SR, Portlock DE (2001) Curr Opin Chem Biol 5:273
Roehrig S, Straub A, Pohlmann J, Lampe T, Pernerstorfer J, Schlemmer KH, Reinemer P, Perzborn E (2005) J Med Chem 48:5900
Paolini GV, Shapland RHB, van Hoorn WP, Masonh JS, Hopkins AL (2006) Nat Biotech 24:805
Kingston DGI (1996) In: Wermuth CG (ed) The Practice of Medicinal Chemistry. Academic, London, pp 101–116
Butler MS (2004) J Nat Prod 67:2141
Newman DJ, Cragg GM, Snader KM (2003) J Nat Prod 66:1022
Cragg GM, Newman DJ, Snader KM (1997) J Nat Prod 60:52
Shu YZ (1998) J Nat Prod 61:1053
Henkel T, Brunne RM, Müller H, Reichel F (1999) Angew Chem Int Ed 38:643
Lee ML, Schneider G (2001) J Comb Chem 3:284
Mann J (2002) Nat Rev Cancer 2:143
Clardy J, Walsh C (2004) Nature 432:829
Walsh CT (2005) Nat Chem Biol 1:122
Koehn FE, Carter GT (2005) Nat Rev Drug Disc 4:206
von Nussbaum F, Brands M, Hinzen B, Weigand S, Häbich D (2006) Angew Chem Int Ed 45:5072
Zaragoza-Dörwald F (2002) Organic Synthesis on Solid Phase, 2nd edn. Wiley, Weinheim
Reggelin M, Brenig V, Zur C (2000) Org Lett 2:531
Paterson I, Gottschling D, Menche D (2005) Chem Commun 3568
Paterson I, Donghi M, Gerlach K (2000) Angew Chem Int Ed 39:3315
Barun O, Sommer S, Waldmann H (2004) Angew Chem Int Ed 43:3195
Leßmann T, Waldmann H (2006) Chem Commun 3380
Nad S, Breinbauer R (2004) Angew Chem Int Ed 43:2297
Nad S, Roller S, Haag R, Breinbauer R (2005) Org Lett 8:403
Spencer RW (1998) Biotechnol Bioeng 61:61
Watson C (1999) Angew Chem Int Ed 38:1903
Mason JS, Hermsmeier MA (1999) Curr Opin Chem Biol 3:342
Wilson LJ (2000) In: Burgess K (ed) Solid-Phase Organic Synthesis. Wiley, New York, pp 247–267
Wessjohann LA (2000) Curr Opin Chem Biol 4:303
Arya P, Baek MG (2001) Curr Opin Chem Biol 5:292
Hall DG, Manku S, Wang F (2001) J Comb Chem 3:125
Nicolaou KC, Pfefferkorn JA (2001) Biopolymers 60:171
Nielsen J (2002) Curr Opin Chem Biol 6:297
Breinbauer R, Manger M, Scheck M, Waldmann H (2002) Curr Med Chem 9:2129
Abel U, Koch C, Speitling M, Hansske FG (2002) Curr Opin Chem Biol 6:453
Ganesan A (2002) Drug Discov Today 7:47
Knepper K, Gil C, Bräse S (2003) Comb Chem High Throughput Screen 6:673
Abreu PM, Branco PS (2003) J Braz Chem Soc 14:675
Boldi AM (2004) Curr Opin Chem Biol 8:281
Shang S, Tan DS (2005) Curr Opin Chem Biol 9:248
Reayi A, Arya P (2005) Curr Opin Chem Biol 9:240
Messer R, Fuhrer CA, Häner R (2005) Curr Opin Chem Biol 9:259
Wessjohann LA, Ruijter E (2005) Topics Curr Chem 243:137
Sommer S, Breinbauer R, Waldmann H (2002) In: Schmalz HG, Wirth T (eds) Organic Synthesis Highlights V. Wiley, Weinheim, p 395
Seeberger P (2002) Curr Opin Chem Biol 6:289
Dolle RE, Le Bourdonnec B, Morales GA, Moriarty KJ, Salvino JM (2006) J Comb Chem 8:599
Dolle RE (2005) J Comb Chem 7:739
Dolle RE (2004) J Comb Chem 6:623
Dolle RE (2003) J Comb Chem 5:693
Dolle RE (2002) J Comb Chem 4:369
Dolle RE (2001) J Comb Chem 3:477
Dolle RE (2000) J Comb Chem 2:383
Dolle RE (2000) J Comb Chem 1:235
Dolle RE (1998) Mol Div 3:199
Dolle RE (1998) Mol Div 3:233
Meseguer B, Alonso-Diaz D, Griebenow N, Herget T, Waldmann H (1999) Angew Chem Int Ed 38:2902
Xiao YX, Parandoosh Z, Nova MP (1997) J Org Chem 62:6029
Nicolaou KC, Winssinger N, Vourloumis D, Ohshima T, Kim S, Pfefferkorn J, Xu JY, Li T (1998) J Am Chem Soc 120:10814
Akritopoulou-Zanze I, Sowin TJ (2001) J Comb Chem 3:301
Xu R, Greiveldinger G, Marenus LE, Cooper A, Ellman JA (1999) J Am Chem Soc 121:4898
Nicolaou KC, Winssinger N, Hughes R, Smethurst C, Cho SY (2000) Angew Chem Int Ed 39:1984
Nicolaou KC, Pastor J, Winssinger N, Murphy F (1998) J Am Chem Soc 120:5132
Nicolaou KC, Winssinger N, Pastor J, Murphy F (1998) Angew Chem Int Ed 37:2534
Jimenez JC, Chavarria B, Lopez-Macia A, Royo M, Giralt E, Albericio F (2003) Org Lett 5:2115
Zenkoh T, Hatori H, Tanaka H, Hasegawa M, Hatakeyama M, Kabe Y, Sato H, Kawaguchi H, Handa H, Takahashi H (2004) Org Lett 6:2477
Doi T, Hijikuro I, Takahashi T (1999) J Am Chem Soc 121:6749
Hijikuro I, Doi T, Takahashi T (2001) J Am Chem Soc 123:3716
Barluenga S, Moulin E, Lopez P, Winssinger N (2005) Chem Eur J 11:4935
Barluenga S, Dakas PY, Ferandin Y, Meijer L, Winssinger N (2006) Angew Chem Int Ed 45:3951
Reiser U, Jauch J (2001) Synlett 90
Wang H, Ganesan A (1999) Org Lett 1:1647
Wang H, Ganesan A (2000) J Comb Chem 2:186
van Loevezijn A, van Maarseveen JH, Stegman K, Visser GM, Koomen GJ (1998) Tetrahedron Lett 39:4737
You SL, Deechongkit S, Kelly JW (2004) Org Lett 6:2627
Nicolaou KC, Winssinger N, Pastor J, Ninkovic S, Sarabia F, He Y, Vourloumis D, Yang Z, Li T, Giannakakou P, Hamel E (1997) Nature 387:268
Crowley JI, Rapoport H (1970) J Am Chem Soc 92:6363
Schürer SC, Blechert S (1999) Synlett 879
Seitz O (2001) Nachr Chem 49:312
Nicolaou KC, Vourloumis D, Li T, Pastor J, Winssinger N, He Y, Ninkovic S, Sarabia F, Vallberg H, Roschangar F, King NP, Finlay MRV, Giannakakou P, Verdier-Panard P, Hamel E (1997) Angew Chem Int Ed 36:2097
Thompson LA, Moore FL, Moon YC, Ellman JA (1998) J Org Chem 63:2066
Dragoli DR, Thompson LA, O'Brien J, Ellman JA (1999) J Comb Chem 1:534
Lee KJ, Angulo A, Ghazal P, Janda KD (1999) Org Lett 1:1859
Brohm D, Metzger S, Bhargava A, Müller O, Lieb F, Waldmann H (2002) Angew Chem Int Ed 41:307
Brohm D, Philippe N, Metzger S, Bhargava A, Müller O, Lieb F, Waldmann H (2002) J Am Chem Soc 124:13171
Takahashi T, Kusaka SI, Doi T, Sunazuka T, Omura S (2003) Angew Chem Int Ed 42:5230
Leitheiser CJ, Smith KL, Rishel MJ, Hashimoto S, Konishi K, Thomas CJ, Li C, McCormick MM, Hecht SM (2003) J Am Chem Soc 125:8218
Pelish HE, Westwood NJ, Feng Y, Kirchhausen T, Shair MD (2001) J Am Chem Soc 123:6740
Pelish HE, Peterson JR, Salvarezaa SB, Rodriguez-Boulan E, Chen JL, Stamnes M, Macia E, Feng Y, Shair MD, Kirchhausen T (2006) Nat Chem Biol 2:39
Lindsley CW, Chan LK, Goess BC, Joseph R, Shair MD (2000) J Am Chem Soc 122:422
Goess BC, Hannoush RN, Chan LK, Kirchhausen T, Shair MD (2006) J Am Chem Soc 128:5391
Marfil M, Albericio F, Alvarez M (2004) Tetrahedron 60:8659
Myers AG, Lanman BA (2002) J Am Chem Soc 124:12969
Evans BE, Rittle KE, Bock MG, DiPrado RM, Freidinger RM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RSL, Lotti VJ, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J (1988) J Med Chem 31:2235
Costantino L, Barlocco D (2006) Curr Med Chem 13:65
Patchett AA, Nargund RP (2000) Ann Rep Med Chem 35:289
Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao GQ, Barluenga S, Mitchell HJ (2000) J Am Chem Soc 122:9939
Nicolaou KC, Pfefferkorn JA, Mitchell HJ, Roecker AJ, Barluenga S, Cao GQ, Lillig JE (2000) J Am Chem Soc 122:9954
Nicolaou KC, Pfefferkorn JA, Schuler F, Roecker AJ, Cao GQ, Casida JE (2000) Chem Biol 7:979
Koch MA, Schuffenhauer A, Scheck M, Casaulta M, Odermatt A, Waldmann H (2005) Proc Natl Acad Sci USA 102:17272
Arve L, Voigt T, Waldmann H (2006) QSAR Comb Sci 25:449
Nören-Müller A, Reis-Correa I Jr, Prinz H, Rosenbaum C, Saxena K, Schwalbe HJ, Vestweber D, Cagna G, Schunk S, Schwarz O, Schiewe J, Waldmann H (2006) Proc Natl Acad Sci USA 103:10606
Norman TC, Gray NS, Koh JT, Schultz PG (1996) J Am Chem Soc 118:7430
Ding S, Gray NS, Ding Q, Schultz PG (2001) J Org Chem 66:8273
Ding S, Gray NS, Wu X, Ding Q, Schultz PG (2002) J Am Chem Soc 124:1594
Sanz MA, Voigt T, Waldmann H (2006) Adv Synth Catal 348:1511
Zhonghong G, Reddy PT, Quevillon S, Couve-Bonnaire S, Arya P (2005) Angew Chem Int Ed 44:1366
Knepper K, Ziegert RE, Bräse S (2004) 60:8591
Baxendale IR, Ley SV (2002) Nat Rev Drug Discov 1:573
Baxendale IR, Ley SV, Piutti C (2002) Angew Chem Int Ed 41:2194
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Mentel, M., Breinbauer, R. (2007). Combinatorial Solid-Phase Natural Product Chemistry. In: Bräse, S. (eds) Combinatorial Chemistry on Solid Supports. Topics in Current Chemistry, vol 278. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2006_107
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DOI: https://doi.org/10.1007/128_2006_107
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