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Solid Phase Chemistry for the Directed Synthesis of Biologically Active Polyamine Analogs, Derivatives, and Conjugates

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Combinatorial Chemistry on Solid Supports

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 278))

Abstract

Polyamines in naturally occurring compounds are biologically active molecules that do not display a great diversity but are very abundant in almost all organisms. Their functions comprise antibiotics, immunosuppressants, toxins, and many others. In most biologically active compounds the polyamine chain is coupled to other functionalities making the polyamine an excellent template for solid phase chemistry and combinatorial approaches. This review comprises common techniques for the synthesis of polyamines and polyamine derivatives on solid support. It includes the description of basic synthesis requirements such as of suitable resins, new linkers, reaction conditions for generation of biologically active polyamines and polyamines in natural products as well as the description of protection groups. Moreover, it will focus on the modular coupling of the amine building blocks using different synthesis strategies. Thus, the advantages of performing reactions on polymer-supported substrates in terms of avoiding side reactions and facilitating product/metal separation are highlighted.

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References

  1. Karigiannis G, Papaioannou D (2000) Eur J Org Chem 10:1841

    Google Scholar 

  2. Gerner EW, Meyskens FL Jr (2004) Nat Rev Cancer 4:781

    CAS  Google Scholar 

  3. Wang Y, Murray-Stewart T, Devereux W, Hacker A, Frydman B, Woster PM, Casero RA Jr (2003) Biochem Biophys Res Commun 304:605

    CAS  Google Scholar 

  4. Wang Y, Casero RA Jr (2006) J Biochem (Tokyo) 139:17

    CAS  Google Scholar 

  5. Milovic V (2001) Eur J Gastroenterol Hepatol 13:1021

    CAS  Google Scholar 

  6. Cohen SS (1998) A guide to the polyamines. Oxford University Press, New York

    Google Scholar 

  7. Milovic V, Faust D, Turchanowa L, Stein J, Caspary WF (2001) Nutrition 17:462

    CAS  Google Scholar 

  8. Flock S, Houssier C (1997) J Biomol Struct Dyn 15:53

    CAS  Google Scholar 

  9. Bloomfield VA (1991) Biopolymers 31:1471

    CAS  Google Scholar 

  10. Tabor CW, Tabor H (1984) Annu Rev Biochem 53:749

    CAS  Google Scholar 

  11. Hougaard DM, Bolund L, Fujiwara K, Larsson LI (1987) Eur J Cell Biol 44:151

    CAS  Google Scholar 

  12. Oller AR, Vanden Broek W, Conrad M, Topal MD (1991) Biochemistry 30:2543

    CAS  Google Scholar 

  13. Vial L, Ludlow RF, Leclaire J, Perez-Fernandez R, Otto S (2006) J Am Chem Soc 128:10253

    CAS  Google Scholar 

  14. Luly JR (1991) Annu Rep Med Chem 26:211

    CAS  Google Scholar 

  15. Ganem B (1982) Acc Chem Res 15:290

    CAS  Google Scholar 

  16. Moore KS, Wehrli S, Roder H, Rogers M, Forrest JN Jr, McCrimmon D, Zasloff M (1993) Proc Natl Acad Sci 90:1354

    CAS  Google Scholar 

  17. Kurylo-Borowska Z, Heaney-Kieras J (1983) Methods Enzymol 94:441

    Article  CAS  Google Scholar 

  18. Choi SK, Nakanishi K, Usherwood PNR (1993) Tetrahedron 49:5777

    CAS  Google Scholar 

  19. Bycroft BW, Chan WC, Hone ND, Millington S, Nash IA (1994) J Am Chem Soc 116:7415

    CAS  Google Scholar 

  20. Bienz S, Bisegger P, Guggisberg A, Hesse M (2005) Nat Prod Rep 22:647

    CAS  Google Scholar 

  21. Stromgaard K, Andersen K, Krogsgaard-Larsen P, Jaroszewski JW (2001) Mini Rev Med Chem 1:317

    CAS  Google Scholar 

  22. Huang Y, Pledgie A, Casero RA Jr, Davidson NE (2005) Anticancer Drugs 16:229

    CAS  Google Scholar 

  23. Kan T, Fukuyama T (2004) Chem Commun 4:353

    Google Scholar 

  24. Kan T, Kobayashi H, Fukuyama T (2002) Synlett 8:1338

    Google Scholar 

  25. Pringle AK, Morrison B III, Bradley M, Iannotti F, Sundstrom LE (2003) Naunyn Schmiedebergs Arch Pharmacol 368:216

    CAS  Google Scholar 

  26. Morrison B III, Pringle AK, McManus T, Ellard J, Bradley M, Signorelli F, Iannotti F, Sundstrom LE (2002) Br J Pharmacol 137:1255

    CAS  Google Scholar 

  27. Smith HK, Bradley M (1999) J Comb Chem 1:326

    CAS  Google Scholar 

  28. Marsh IR, Smith HK, Leblanc C, Bradley M (1997) Mol Divers 2:165

    CAS  Google Scholar 

  29. Manku S, Wang F, Hall DG (2003) J Comb Chem 5:379

    CAS  Google Scholar 

  30. Manku S, Laplante C, Kopac D, Chan T, Hall DG (2001) J Org Chem 66:874

    CAS  Google Scholar 

  31. Manku S, Hall DG (2006) J Comb Chem 8:551

    CAS  Google Scholar 

  32. Feuerstein BG, Williams LD, Basu HS, Marton LJ (1991) J Cell Biochem 46:37

    CAS  Google Scholar 

  33. Thomas TJ, Messner RP (1988) J Mol Biol 201:463

    CAS  Google Scholar 

  34. Geall AJ, Taylor RJ, Earll ME, Eaton MA, Blagbrough IS (2000) Bioconjug Chem 11:314

    CAS  Google Scholar 

  35. Rich A, Zhang S (2003) Nat Rev Genet 4:566

    CAS  Google Scholar 

  36. D'Agostino L, di Pietro M, Di Luccia A (2005) Febs J 272:3777

    Google Scholar 

  37. Esposito D, DelVecchio P, Barone G (1997) J Am Chem Soc 119:2606

    CAS  Google Scholar 

  38. Khan AU, Di Mascio P, Medeiros MH, Wilson T (1992) Proc Natl Acad Sci USA 89:11428

    CAS  Google Scholar 

  39. Baeza I, Gariglio P, Rangel LM, Chavez P, Cervantes L, Arguello C, Wong C, Montanez C (1987) Biochemistry 26:6387

    CAS  Google Scholar 

  40. Kuosmanen M, Poso H (1985) FEBS Lett 179:17

    CAS  Google Scholar 

  41. Pingoud A, Urbanke C, Alves J, Ehbrecht HJ, Zabeau M, Gualerzi C (1984) Biochemistry 23:5697

    CAS  Google Scholar 

  42. Oana H, Tsumoto K, Yoshikawa Y, Yoshikawa K (2002) FEBS Lett 530:143

    CAS  Google Scholar 

  43. Kusama-Eguchi K, Watanabe S, Irisawa M, Watanabe K, Igarashi K (1991) Biochem Biophys Res Commun 177:745

    CAS  Google Scholar 

  44. Kusama-Eguchi K, Irisawa M, Watanabe S, Watanabe K, Igarashi K (1991) Arch Biochem Biophys 288:495

    CAS  Google Scholar 

  45. Frydman B, Westler WM, Samejima K (1996) J Org Chem 61:2588

    CAS  Google Scholar 

  46. Tropp JS, Redfield AG (1983) Nucleic Acids Res 11:2121

    CAS  Google Scholar 

  47. Hamachi I, Yamada Y, Eboshi R, Hiraoka T, Shinkai S (1999) Bioorg Med Chem Lett 9:1215

    CAS  Google Scholar 

  48. Kuimelis RG, McLaughlin LW (1996) Biochemistry 35:5308

    CAS  Google Scholar 

  49. Hammann C, Hormes R, Sczakiel G, Tabler M (1997) Nucleic Acids Res 25:4715

    CAS  Google Scholar 

  50. Olive JE, Collins RA (1998) Biochemistry 37:6476

    CAS  Google Scholar 

  51. Earnshaw DJ, Gait MJ (1999) Nucleic Acids Symp Ser 42:273

    CAS  Google Scholar 

  52. Earnshaw DJ, Gait MJ (1998) Nucleic Acids Res 26:5551

    CAS  Google Scholar 

  53. Welz R, Schmidt C, Muller S (2001) Biochem Biophys Res Commun 283:648

    CAS  Google Scholar 

  54. Fouace S, Gaudin C, Picard S, Corvaisier S, Renault J, Carboni B, Felden B (2004) Nucleic Acids Res 32:151

    CAS  Google Scholar 

  55. Marsh AJ, Williams DM, Grasby JA (2004) Org Biomol Chem 2:2103

    CAS  Google Scholar 

  56. Panagiotidis CA, Artandi S, Calame K, Silverstein SJ (1995) Nucleic Acids Res 23:1800

    CAS  Google Scholar 

  57. Thomas T, Thomas TJ (2001) Cell Mol Life Sci 58:244

    CAS  Google Scholar 

  58. Chen Y, Kramer DL, Diegelman P, Vujcic S, Porter CW (2001) Cancer Res 61:6437

    CAS  Google Scholar 

  59. Faaland CA, Thomas TJ, Balabhadrapathruni S, Langer T, Mian S, Shirahata A, Gallo MA, Thomas T (2000) Biochem Cell Biol 78:415

    CAS  Google Scholar 

  60. Hu RH, Pegg AE (1997) Biochem J 328:307

    CAS  Google Scholar 

  61. Brana MF, Ramos A (2001) Curr Med Chem Anticancer Agents 1:237

    CAS  Google Scholar 

  62. Adlam G, Blagbrough IS, Taylor S, Latham HC, Haworth IS, Rodger A (1994) Bioorg Med Chem Lett 4:2435

    CAS  Google Scholar 

  63. Rodger A, Blagbrough IS, Adlam G, Carpenter ML (1994) Biopolymers 34:1583

    CAS  Google Scholar 

  64. Rodger A, Taylor S, Adlam G, Blagbrough IS, Haworth IS (1995) Bioorg Med Chem 3:861

    CAS  Google Scholar 

  65. Li YL, Eiseman JL, Sentz DL, Rogers FA, Pan SS, Hu LT, Egorin MJ, Callery PS (1996) J Med Chem 39:339

    CAS  Google Scholar 

  66. Johnson TD (1996) Trends Pharmacol Sci 17:22

    CAS  Google Scholar 

  67. Williams K (1995) Neurosci Lett 184:181

    CAS  Google Scholar 

  68. Armstrong D, Neu H, Peterson LR, Tomasz A (1995) Microb Drug Resist 1:1

    CAS  Google Scholar 

  69. Tomasz A (1994) N Engl J Med 330:1247

    CAS  Google Scholar 

  70. Kikuchi K, Bernard EM, Sadownik A, Regen SL, Armstrong D (1997) Antimicrob Agents Chemother 41:1433

    CAS  Google Scholar 

  71. van't Hof W, Veerman ECI, Helmerhorst EJ, Amerongen AVN (2001) Biol Chem 382:597

    Google Scholar 

  72. Blagbrough IS, Geall AJ, David SA (2000) Bioorg Med Chem Lett 10:1959

    CAS  Google Scholar 

  73. David SA, Silverstein R, Amura CR, Kielian T, Morrison DC (1999) Antimicrob Agents Chemother 43:912

    CAS  Google Scholar 

  74. Miller KA, Kumar EVKS, Wood SJ, Cromer JR, Datta A, David SA (2005) J Med Chem 48:2589

    CAS  Google Scholar 

  75. Mayo KH (2000) Trends Biotechnol 18:212

    CAS  Google Scholar 

  76. Scott MG, Hancock REW (2000) Crit Rev Immunol 20:407

    CAS  Google Scholar 

  77. Scott MG, Vreugdenhil ACE, Buurman WA, Hancock REW, Gold M (2000) J Immunol 164:549

    CAS  Google Scholar 

  78. Jackson JJ, Kropp H, Hurley JC (1994) J Infect Dis 169:471

    CAS  Google Scholar 

  79. Prins JM, Kuijper EJ, Mevissen MLCM, Speelman P, Vandeventer SJH (1995) Infect Immun 63:2236

    CAS  Google Scholar 

  80. Prins JM, Vandeventer SJH, Kuijper EJ, Speelman P (1994) Antimicrob Agents Chemother 38:1211

    CAS  Google Scholar 

  81. Chen WH, Shao XB, Moellering R, Wennersten C, Regen SL (2006) Bioconjug Chem 17:1582

    CAS  Google Scholar 

  82. Brunel JM, Salmi C, Loncle C, Vidal N, Letourneux Y (2005) Curr Cancer Drug Targets 5:267

    CAS  Google Scholar 

  83. Savage PB, Li C, Taotafa U, Ding B, Guan Q (2002) FEMS Microbiol Lett 217:1

    CAS  Google Scholar 

  84. Janout V, Jing B, Regen SL (2002) Bioconjug Chem 13:351

    CAS  Google Scholar 

  85. Janout V, Jing B, Staina IV, Regen SL (2003) J Am Chem Soc 125:4436

    CAS  Google Scholar 

  86. Janout V, Zhang LH, Staina IV, Di Giorgio C, Regen SL (2001) J Am Chem Soc 123:5401

    CAS  Google Scholar 

  87. Janout V, Staina IV, Bandyopadhyay P, Regen SL (2001) J Am Chem Soc 123:9926

    CAS  Google Scholar 

  88. Ponasik JA, Conova S, Kinghorn D, Kinney WA, Rittschof D, Ganem B (1998) Tetrahedron 54:6977

    CAS  Google Scholar 

  89. Tsukamoto S, Kato H, Hirota H, Fusetani N (1996) Tetrahedron Lett 37:5555

    CAS  Google Scholar 

  90. Tsukamoto S, Kato H, Hirota H, Fusetani N (1996) J Org Chem 61:2936

    CAS  Google Scholar 

  91. Ohtani I, Kusumi T, Kakisawa H, Kashman Y, Hirsh S (1992) J Am Chem Soc 114:8472

    CAS  Google Scholar 

  92. Kong Thoo Lin P, Dance AM, Bestwick C, Milne L (2003) Biochem Soc Trans 31:407

    CAS  Google Scholar 

  93. Kuksa VA, Pavlov VA, Kong Thoo Lin P (2002) Bioorg Med Chem 10:691

    CAS  Google Scholar 

  94. Cordeiro-da-Silva A, Tavares J, Araujo N, Cerqueira F, Tomas A, Kong Thoo Lin P, Ouaissi A (2004) Int Immunopharmacol 4:547

    CAS  Google Scholar 

  95. Pavlov V, Rodilla V, Kong Thoo Lin P (2002) Life Sci 71:1161

    CAS  Google Scholar 

  96. Pavlov V, Kong Thoo Lin P, Rodilla V (2001) Chem Biol Interact 137:15

    CAS  Google Scholar 

  97. Chantrapromma K, Mcmanis JS, Ganem B (1980) Tetrahedron Lett 21:2605

    CAS  Google Scholar 

  98. Chantrapromma K, Mcmanis JS, Ganem B (1980) Tetrahedron Lett 21:2475

    CAS  Google Scholar 

  99. Melocoton TL, Kamil ES, Cohen AH, Fine RN (1991) Am J Kidney Dis 18:583

    CAS  Google Scholar 

  100. Verschoyle RD, Carthew P, Holley JL, Cullis P, Cohen GM (1994) Cancer Lett 85:217

    CAS  Google Scholar 

  101. Chen Y, Kramer DL, Jell J, Vujcic S, Porter CW (2003) Mol Pharmacol 64:1153

    CAS  Google Scholar 

  102. Seghieri G, Anichini R, Ciuti M, Gironi A, Bennardini F, Franconi F (1997) Diabetes Res Clin Pract 37:15

    CAS  Google Scholar 

  103. Russell DH, Stern LZ (1979) Trans Am Neurol Assoc 104:123

    CAS  Google Scholar 

  104. Russell DH, Stern LZ (1981) Neurology 31:80

    CAS  Google Scholar 

  105. Russell DH, Rosenblum MG, Beckerman RC, Durie BG, Taussig LM, Barnett DR (1979) Pediatr Res 13:1137

    Article  CAS  Google Scholar 

  106. Ignatenko NA, Yerushalmi HF, Watts GS, Futscher BW, Stringer DE, Marton LJ, Gerner EW (2006) Technol Cancer Res Treat 5:553

    CAS  Google Scholar 

  107. Basuroy UK, Gerner EW (2006) J Biochem (Tokyo) 139:27

    CAS  Google Scholar 

  108. Mitchell JL, Leyser A, Holtorff MS, Bates JS, Frydman B, Valasinas AL, Reddy VK, Marton LJ (2002) Biochem J 366:663

    CAS  Google Scholar 

  109. Petros LM, Graminski GF, Robinson S, Burns MR, Kisiel N, Gesteland RF, Atkins JF, Kramer DL, Howard MT, Weeks RS (2006) J Biochem (Tokyo) 140:657

    CAS  Google Scholar 

  110. Takahashi Y, Mai M, Nishioka K (2000) Int J Cancer 85:243

    CAS  Google Scholar 

  111. Takigawa M, Enomoto M, Nishida Y, Pan HO, Kinoshita A, Suzuki F (1990) Cancer Res 50:4131

    CAS  Google Scholar 

  112. Marton LJ, Pegg AE (1995) Annu Rev Pharmacol Toxicol 35:55

    CAS  Google Scholar 

  113. Porter CW, Sufrin JR (1986) Anticancer Res 6:525

    CAS  Google Scholar 

  114. Casero RA Jr, Pegg AE (1993) FASEB J 7:653

    CAS  Google Scholar 

  115. Bergeron RJ, Neims AH, McManis JS, Hawthorne TR, Vinson JR, Bortell R, Ingeno MJ (1988) J Med Chem 31:1183

    CAS  Google Scholar 

  116. Saab NH, West EE, Bieszk NC, Preuss CV, Mank AR, Casero RA Jr, Woster PM (1993) J Med Chem 36:2998

    CAS  Google Scholar 

  117. Valasinas A, Reddy VK, Blokhin AV, Basu HS, Bhattacharya S, Sarkar A, Marton LJ, Frydman B (2003) Bioorg Med Chem 11:4121

    CAS  Google Scholar 

  118. Reddy VK, Valasinas A, Sarkar A, Basu HS, Marton LJ, Frydman B (1998) J Med Chem 41:4723

    CAS  Google Scholar 

  119. Bacchi CJ, Weiss LM, Lane S, Frydman B, Valasinas A, Reddy V, Sun JS, Marton LJ, Khan IA, Moretto M, Yarlett N, Wittner M (2002) Antimicrob Agents Chemother 46:55

    CAS  Google Scholar 

  120. Valasinas A, Sarkar A, Reddy VK, Marton LJ, Basu HS, Frydman B (2001) J Med Chem 44:390

    CAS  Google Scholar 

  121. Casero RA Jr, Woster PM (2001) J Med Chem 44:1

    CAS  Google Scholar 

  122. Porter CW, Berger FG, Pegg AE, Ganis B, Bergeron RJ (1987) Biochem J 242:433

    CAS  Google Scholar 

  123. Wolff AC, Armstrong DK, Fetting JH, Carducci MK, Riley CD, Bender JF, Casero RA Jr, Davidson NE (2003) Clin Cancer Res 9:5922

    CAS  Google Scholar 

  124. Hahm HA, Dunn VR, Butash KA, Deveraux WL, Woster PM, Casero RA Jr, Davidson NE (2001) Clin Cancer Res 7:391

    CAS  Google Scholar 

  125. Wu R, Saab NH, Huang H, Wiest L, Pegg AE, Casero RA Jr, Woster PM (1996) Bioorg Med Chem 4:825

    CAS  Google Scholar 

  126. Webb HK, Wu Z, Sirisoma N, Ha HC, Casero RA Jr, Woster PM (1999) J Med Chem 42:1415

    CAS  Google Scholar 

  127. Nairn LM, Lindsay GS, Woster PM, Wallace HM (2000) J Cell Physiol 182:209

    CAS  Google Scholar 

  128. Huang CC, Hall DH, Hedgecock EM, Kao G, Karantza V, Vogel BE, Hutter H, Chisholm AD, Yurchenco PD, Wadsworth WG (2003) Development 130:3343

    CAS  Google Scholar 

  129. Basu HS, Sturkenboom MC, Delcros JG, Csokan PP, Szollosi J, Feuerstein BG, Marton LJ (1992) Biochem J 282(3):723

    CAS  Google Scholar 

  130. Casero RA Jr, Go B, Theiss HW, Smith J, Baylin SB, Luk GD (1987) Cancer Res 47:3964

    CAS  Google Scholar 

  131. Bergeron RJ, Feng Y, Weimar WR, McManis JS, Dimova H, Porter C, Raisler B, Phanstiel O (1997) J Med Chem 40:1475

    CAS  Google Scholar 

  132. Edwards ML, Prakash NJ, Stemerick DM, Sunkara SP, Bitonti AJ, Davis GF, Dumont JA, Bey P (1990) J Med Chem 33:1369

    CAS  Google Scholar 

  133. Igarashi K, Koga K, He Y, Shimogori T, Ekimoto H, Kashiwagi K, Shirahata A (1995) Cancer Res 55:2615

    CAS  Google Scholar 

  134. Ha HC, Woster PM, Yager JD, Casero RA Jr (1997) Proc Natl Acad Sci USA 94:11557

    CAS  Google Scholar 

  135. Hosseinkhani H, Aoyama T, Ogawa O, Tabata Y (2003) J Control Release 88:297

    CAS  Google Scholar 

  136. Geall AJ, Blagbrough IS (2000) J Pharm Biomed Anal 22:849

    CAS  Google Scholar 

  137. Remy JS, Sirlin C, Vierling P, Behr JP (1994) Bioconjug Chem 5:647

    CAS  Google Scholar 

  138. Moradpour D, Schauer JI, Zurawski VR Jr, Wands JR, Boutin RH (1996) Biochem Biophys Res Commun 221:82

    CAS  Google Scholar 

  139. Geall AJ, Blagbrough IS (1998) Tetrahedron Lett 39:443

    CAS  Google Scholar 

  140. Geall AJ, Al-Hadithi D, Blagbrough IS (1998) Chem Commun 18:2035

    Google Scholar 

  141. Geall AJ, Taylor RJ, Earll ME, Eaton MAW, Blagbrough IS (1998) Chem Commun 13:1403

    Google Scholar 

  142. Cooper RG, Etheridge CJ, Stewart L, Marshall J, Rudginsky S, Cheng SH, Miller AD (1998) Chem Eur J 4:137

    Google Scholar 

  143. Merritt MA, Regen SL (1998) Abstr Pap Am Chem Soc 216:U372

    Google Scholar 

  144. Blagbrough IS, Geall AJ (1998) Tetrahedron Lett 39:439

    CAS  Google Scholar 

  145. Ahmed OA, Adjimatera N, Pourzand C, Blagbrough IS (2005) Pharm Res 22:972

    CAS  Google Scholar 

  146. Vijayanathan V, Thomas T, Thomas TJ (2002) Biochemistry 41:14085

    CAS  Google Scholar 

  147. Golan R, Pietrasanta LI, Hsieh W, Hansma HG (1999) Biochemistry 38:14069

    CAS  Google Scholar 

  148. Wiethoff CM, Middaugh CR (2003) J Pharm Sci 92:203

    CAS  Google Scholar 

  149. Cho YW, Kim JD, Park K (2003) J Pharm Pharmacol 55:721

    CAS  Google Scholar 

  150. Yingyongnarongkul BE, Howarth M, Elliott T, Bradley M (2004) J Comb Chem 6:753

    CAS  Google Scholar 

  151. Yingyongnarongkul BE, Howarth M, Elliott T, Bradley M (2004) Chemistry 10:463

    CAS  Google Scholar 

  152. Marsh IR, Smith H, Bradley M (1996) Chem Commun 8:941

    Google Scholar 

  153. Conti P, Demont D, Cals J, Ottenheijm HCJ, Leysen D (1997) Tetrahedron Lett 38:2915

    CAS  Google Scholar 

  154. Brown EG, Nuss JM (1997) Tetrahedron Lett 38:8457

    CAS  Google Scholar 

  155. Katritzky AR, Xie LH, Zhang GF, Griffith M, Watson K, Kiely JS (1997) Tetrahedron Lett 38:7011

    CAS  Google Scholar 

  156. Fauchet V, Bourel L, Tarter A, Sergheraert C (1994) Bioorg Med Chem Lett 4:2559

    CAS  Google Scholar 

  157. Overman LE, Okazaki ME, Mishra P (1986) Tetrahedron Lett 27:4391

    CAS  Google Scholar 

  158. Felix AM, Merrifield RB (1970) J Am Chem Soc 92:1385

    CAS  Google Scholar 

  159. Burdick DJ, Struble ME, Burnier JP (1993) Tetrahedron Lett 34:2589

    CAS  Google Scholar 

  160. Bycroft BW, Chan WC, Chhabra SR, Teesdalespittle PH, Hardy PM (1993) J Chem Soc Chem Comm 9:776

    Google Scholar 

  161. Bycroft BW, Chan WC, Chhabra SR, Hone ND (1993) J Chem Soc Chem Comm 9:778

    Google Scholar 

  162. Marsh IR, Bradley M (1997) Tetrahedron 53:17317

    CAS  Google Scholar 

  163. Marsh IR, Smith HK, LeBlanc C, Bradley M (1997) Mol Divers 2:165

    CAS  Google Scholar 

  164. Tomasi S, Picard S, Laine C, Babonneau V, Goujeon A, Boustie J, Uriac P (2006) J Comb Chem 8:11

    CAS  Google Scholar 

  165. Byk G, Frederic M, Scherman D (1997) Tetrahedron Lett 38:3219

    CAS  Google Scholar 

  166. Schröder T, Schmitz K, Niemeier N, Balaban TS, Krug HF, Schepers U, Bräse S (2007) Bioconjug Chem 18:342

    Google Scholar 

  167. Hone ND, Payne LJ (2000) Tetrahedron Lett 41:6149

    CAS  Google Scholar 

  168. Adams JH, Cook RM, Hudson D, Jammalamadaka V, Lyttle MH, Songster MF (1998) J Org Chem 63:3706

    CAS  Google Scholar 

  169. Dixit DM, Leznoff CC (1978) Isr J Chem 17:248

    CAS  Google Scholar 

  170. Raju B, Kogan TP (1997) Tetrahedron Lett 38:3373

    CAS  Google Scholar 

  171. Ho CY, Kukla MJ (1997) Tetrahedron Lett 38:2799

    CAS  Google Scholar 

  172. Hauske JR, Dorff P (1995) Tetrahedron Lett 36:1589

    CAS  Google Scholar 

  173. Tomasi S, Le Roch M, Renault J, Corbel JC, Uriac P, Carboni B, Moncoq D, Martin B, Delcros JG (1998) Bioorg Med Chem Lett 8:635

    CAS  Google Scholar 

  174. Chhabra SR, Khan AN, Bycroft BW (2000) Tetrahedron Lett 41:1095

    CAS  Google Scholar 

  175. Chhabra SR, Khan AN, Bycroft BW (2000) Tetrahedron Lett 41:1099

    CAS  Google Scholar 

  176. Crespo L (2001) In: Martinez J, Fehrentz J-A (eds) Peptides 2000, Proc. 26th European peptide symposium. EDK, Paris

    Google Scholar 

  177. Boojamra CG, Burow KM, Thompson LA, Ellman JA (1997) J Org Chem 62:1240

    CAS  Google Scholar 

  178. Youngman MA, Dax SL (1997) Tetrahedron Lett 38:6347

    CAS  Google Scholar 

  179. Olsen CA, Witt M, Jaroszewski JW, Franzyk H (2003) Org Lett 5:4183

    CAS  Google Scholar 

  180. Schuster M, Pernerstorfer J, Blechert S (1996) Angew Chem Int Edit 35:1979

    CAS  Google Scholar 

  181. Garibay P, Nielsen J, Hoeg-Jensen T (1998) Tetrahedron Lett 39:2207

    CAS  Google Scholar 

  182. Guan YS, Green MA, Bergstrom DE (2000) J Comb Chem 2:297

    CAS  Google Scholar 

  183. Jönsson D, Erlandsson M, Unden A (2001) Tetrahedron Lett 42:6953

    Google Scholar 

  184. Stromgaard K, Andersen K, Ruhland T, Krogsgaard-Larsen P, Jaroszewski JW (2001) Synthesis 6:877

    Google Scholar 

  185. Olsen CA, Witt M, Jaroszewski JW, Franzyk H (2004) Org Lett 6:1935

    CAS  Google Scholar 

  186. Nefzi A, Ostresh JM, Appel JR, Bidlack J, Dooley CT, Houghten RA (2006) Bioorg Med Chem Lett 16:4331

    CAS  Google Scholar 

  187. Nefzi A, Ostresh JM, Yu JP, Houghten RA (2004) J Org Chem 69:3603

    CAS  Google Scholar 

  188. Acharya AN, Nefzi A, Ostresh JM, Houghten RA (2001) J Comb Chem 3:189

    CAS  Google Scholar 

  189. Yu YP, Ostresh JM, Houghten RA (2002) J Org Chem 67:3138

    CAS  Google Scholar 

  190. Acharya AN, Ostresh JM, Houghten RA (2001) J Comb Chem 3:578

    CAS  Google Scholar 

  191. Acharya AN, Ostresh JM, Houghten RA (2002) J Comb Chem 4:214

    CAS  Google Scholar 

  192. Wang F, Manku S, Hall DG (2000) Org Lett 2:1581

    CAS  Google Scholar 

  193. Olsen CA, Witt M, Jaroszewski JW, Franzyk H (2004) J Org Chem 69:6149

    CAS  Google Scholar 

  194. Barlos K, Gatos D, Kutsogianni S, Papaphotiou G, Poulos C, Tsegenidis T (1991) Int J Pept Protein Res 38:562

    Article  CAS  Google Scholar 

  195. Barlos K, Chatzi O, Gatos D, Stavropoulos G (1991) Int J Pept Protein Res 37:513

    CAS  Google Scholar 

  196. Barlos K, Gatos D, Papaphotiou G, Schafer W (1993) Liebigs Ann Chem, p 215

    Google Scholar 

  197. Nash IA, Bycroft BW, Chan WC (1996) Tetrahedron Lett 37:2625

    CAS  Google Scholar 

  198. Barlos K, Gatos D, Kallitsis I, Papaioannou D, Sotiriou P (1988) Liebigs Ann Chem 11:1079

    Google Scholar 

  199. Barlos K, Gatos D, Schafer W (1991) Angew Chem Int Edit 30:590

    Google Scholar 

  200. Hoekstra WJ, Greco MN, Yabut SC, Hulshizer BL, Maryanoff BE (1997) Tetrahedron Lett 38:2629

    CAS  Google Scholar 

  201. Bollhagen R, Schmiedberger M, Barlos K, Grell E (1994) J Chem Soc Chem Comm 22:2559

    Google Scholar 

  202. Jensen KJ, Alsina J, Songster MF, Vagner J, Albericio F, Barany G (1998) J Am Chem Soc 120:5441

    CAS  Google Scholar 

  203. Bettinetti L, Lober S, Hubner H, Gmeiner P (2005) J Comb Chem 7:309

    CAS  Google Scholar 

  204. Swayze EE (1997) Tetrahedron Lett 38:8465

    CAS  Google Scholar 

  205. Fivush AM, Willson TM (1997) Tetrahedron Lett 38:7151

    CAS  Google Scholar 

  206. Aoki Y, Kobayashi S (1999) J Comb Chem 1:371

    Google Scholar 

  207. Kim MS, Diamond SL (2006) Bioorg Med Chem Lett 16:5572

    CAS  Google Scholar 

  208. Kim MS, Diamond SL (2006) Bioorg Med Chem Lett 16:4007

    CAS  Google Scholar 

  209. Pak JK, Guggisberg A, Hesse M (1998) Tetrahedron 54:8035

    CAS  Google Scholar 

  210. Pak JK, Hesse M (1998) Helv Chim Acta 81:2300

    CAS  Google Scholar 

  211. Pak JK, Hesse M (1998) J Org Chem 63:8200

    CAS  Google Scholar 

  212. Adamczyk M, Fishpaugh JR, Heuser KJ (1998) Org Prep Proced Int 30:339

    Article  CAS  Google Scholar 

  213. Olsen CA, Jorgensen MR, Hansen SH, Witt M, Jaroszewski JW, Franzyk H (2005) Org Lett 7:1703

    CAS  Google Scholar 

  214. Page P, Burrage S, Baldock L, Bradley M (1998) Bioorg Med Chem Lett 8:1751

    CAS  Google Scholar 

  215. Marsh IR, Smith H, Bradley M (1996) Chem Commun 8:941

    Google Scholar 

  216. Wellendorph P, Jaroszewski JW, Hansen SH, Franzyk H (2003) Eur J Med Chem 38:117

    CAS  Google Scholar 

  217. Stromgaard K, Bjornsdottir I, Andersen K, Brierley MJ, Rizoli S, Eldursi N, Mellor IR, Usherwood PNR, Hansen SH, Krogsgaard-Larsen P, Jaroszewski JW (2000) Chirality 12:93

    CAS  Google Scholar 

  218. Xu DQ, Prasad K, Repic O, Blacklock TJ (1995) Tetrahedron Lett 36:7357

    CAS  Google Scholar 

  219. Jorgensen MR, Olsen CA, Mellor IR, Usherwood PNR, Witt M, Franzyk H, Jaroszewski JW (2005) J Med Chem 48:56

    CAS  Google Scholar 

  220. Rohwedder B, Mutti Y, Dumy P, Mutter M (1998) Tetrahedron Lett 39:1175

    CAS  Google Scholar 

  221. Lingard I, Bhalay G, Bradley M (2003) Synlett 12:1791

    Google Scholar 

  222. Jönsson D (2002) Tetrahedron Lett 43:4793

    Google Scholar 

  223. Tian ZP, Edwards P, Roeske RW (1992) Int J Pept Protein Res 40:119

    Article  CAS  Google Scholar 

  224. Gao Y, Lane-Bell P, Vederas JC (1998) J Org Chem 63:2133

    CAS  Google Scholar 

  225. Moynihan HA, Yu WP (1998) Synth Commun 28:17

    CAS  Google Scholar 

  226. Alper PB, Hendrix M, Sears P, Wong CH (1998) J Am Chem Soc 120:1965

    CAS  Google Scholar 

  227. Murahashi SI, Naota T, Nakajima N (1987) Chem Lett 5:879

    Google Scholar 

  228. Atwell GJ, Denny WA (1984) Synthesis 12:1032

    Google Scholar 

  229. Manov N, Bienz S (2001) Tetrahedron 57:7893

    CAS  Google Scholar 

  230. Manov N, Tzouros M, Chesnov S, Bigler L, Bienz S (2002) Helv Chim Acta 85:2827

    CAS  Google Scholar 

  231. Karigiannis G, Mamos P, Balayiannis G, Katsoulis I, Papaioannou D (1998) Tetrahedron Lett 39:5117

    CAS  Google Scholar 

  232. Labadie GR, Choi SR, Avery MA (2004) Bioorg Med Chem Lett 14:615

    CAS  Google Scholar 

  233. Kellam B, Bycroft BW, Chan WC, Chhabra SR (1998) Tetrahedron 54:6817

    CAS  Google Scholar 

  234. Kellam B, Bycroft BW, Chhabra SR (1997) Tetrahedron Lett 38:4849

    CAS  Google Scholar 

  235. Kellam B, Chan WC, Chhabra SR, Bycroft BW (1997) Tetrahedron Lett 38:5391

    CAS  Google Scholar 

  236. Chhabra SR, Khan AN, Bycroft BW (1998) Tetrahedron Lett 39:3585

    CAS  Google Scholar 

  237. Osullivan MC, Dalrymple DM (1995) Tetrahedron Lett 36:3451

    CAS  Google Scholar 

  238. Osullivan MC, Zhou QB (1995) Bioorg Med Chem Lett 5:1957

    CAS  Google Scholar 

  239. Sakamoto I, Izumi N, Yamada T, Tsunoda T (2006) Org Lett 8:71

    CAS  Google Scholar 

  240. Fukuyama T, Jow CK, Cheung M (1995) Tetrahedron Lett 36:6373

    CAS  Google Scholar 

  241. Lee CE, Kick EK, Ellman JA (1998) J Am Chem Soc 120:9735

    CAS  Google Scholar 

  242. Kick EK, Roe DC, Skillman AG, Liu GC, Ewing TJA, Sun YX, Kuntz ID, Ellman JA (1997) Chem Biol 4:297

    CAS  Google Scholar 

  243. Fukuyama T, Cheung M, Jow CK, Hidai Y, Kan T (1997) Tetrahedron Lett 38:5831

    CAS  Google Scholar 

  244. Campbell JA, Hart DJ (1993) J Org Chem 58:2900

    CAS  Google Scholar 

  245. Zang EL, Sadler PJ (1997) Synth Commun 27:3145

    CAS  Google Scholar 

  246. Picard S, Le Roch M, Renault J, Uriac P (2004) Org Lett 6:4711

    CAS  Google Scholar 

  247. Morin C, Vidal M (1992) Tetrahedron 48:9277

    CAS  Google Scholar 

  248. Jönsson D, Unden A (2002) Tetrahedron Lett 43:3125

    Google Scholar 

  249. Karigiannis G, Papaioannou D (2000) Eur J Org Chem 10:1841

    Google Scholar 

  250. Ronsin G, Perrin C, Guedat P, Kremer A, Camilleri P, Kirby AJ (2001) Chem Commun 21:2234

    Google Scholar 

  251. Basso A, Bradley M (2003) Tetrahedron Lett 44:2699

    CAS  Google Scholar 

  252. Zuckermann RN, Kerr JM, Kent SBH, Moos WH (1992) J Am Chem Soc 114:10646

    CAS  Google Scholar 

  253. Burkoth TS, Fafarman AT, Charych DH, Connolly MD, Zuckermann RN (2003) J Am Chem Soc 125:8841

    CAS  Google Scholar 

  254. Dankwardt SM, Smith DB, Porco JA, Nguyen CH (1997) Synlett 7:854

    Google Scholar 

  255. Beaver KA, Siegmund AC, Spear KL (1996) Tetrahedron Lett 37:1145

    CAS  Google Scholar 

  256. Bergeron RJ, Huang G, McManis JS, Yao H, Nguyen JN (2005) J Med Chem 48:3099

    CAS  Google Scholar 

  257. Hidai Y, Kan T, Fukuyama T (1999) Tetrahedron Lett 40:4711

    CAS  Google Scholar 

  258. Olsen CA, Franzyk H, Jaroszewski JW (2005) Synthesis 16:2631

    Google Scholar 

  259. Olsen CA, Witt M, Hansen SH, Jaroszewski JW, Franzyk H (2005) Tetrahedron 61:6046

    CAS  Google Scholar 

  260. Sasaki Y, Murphy WA, Heiman ML, Lance VA, Coy DH (1987) J Med Chem 30:1162

    CAS  Google Scholar 

  261. Sasaki Y, Coy DH (1987) Peptides 8:119

    CAS  Google Scholar 

  262. Cantel S, Heitz A, Martinez J, Fehrentz JA (2004) J Pept Sci 10:531

    CAS  Google Scholar 

  263. Vergnon AL, Pottorf RS, Player MR (2004) J Comb Chem 6:91

    CAS  Google Scholar 

  264. Vergnon AL, Pottorf RS, Player MR (2003) Abstr Pap Am Chem S 225:U305

    Google Scholar 

  265. Arya P, Barkley A, Randell KD (2002) J Comb Chem 4:193

    CAS  Google Scholar 

  266. Carrington S, Renault J, Tomasi S, Corbel JC, Uriac P, Blagbrough IS (1999) Chem Commun 14:1341

    Google Scholar 

  267. Fridkin G, Gilon T, Loyter A, Gilon C (2001) J Pept Res 58:36

    CAS  Google Scholar 

  268. Boojamra CG, Burow KM, Ellman JA (1995) J Org Chem 60:5742

    CAS  Google Scholar 

  269. Akamatsu H, Kusumoto S, Fukase K (2002) Tetrahedron Lett 43:8867

    CAS  Google Scholar 

  270. Vassis S, Karigiannis G, Balayiannis G, Militsopoulou M, Mamos P, Francis GW, Papaioannou D (2001) Tetrahedron Lett 42:1579

    CAS  Google Scholar 

  271. Paikoff SJ, Wilson TE, Cho CY, Schultz PG (1996) Tetrahedron Lett 37:5653

    CAS  Google Scholar 

  272. Ostresh JM, Schoner CC, Hamashin VT, Nefzi A, Meyer JP, Houghten RA (1998) J Org Chem 63:8622

    CAS  Google Scholar 

  273. Dubowchik GM, Firestone RA (1996) Tetrahedron Lett 37:6465

    CAS  Google Scholar 

  274. Ferey V, Vedrenne P, Toupet L, LeGall T, Mioskowski C (1996) J Org Chem 61:7244

    CAS  Google Scholar 

  275. Hall DG, Laplante C, Manku S, Nagendran J (1999) J Org Chem 64:698

    CAS  Google Scholar 

  276. Nefzi A, Ostresh JM, Houghten RA (1999) Tetrahedron 55:335

    CAS  Google Scholar 

  277. Nefzi A, Ostresh JM, Giulianotti M, Houghten RA (1999) J Comb Chem 1:195

    CAS  Google Scholar 

  278. Nefzi A, Giulianotti MA, Houghten RA (1999) Tetrahedron Lett 40:8539

    CAS  Google Scholar 

  279. Nefzi A, Giulianotti MA, Ong NA, Houghten RA (2000) Org Lett 2:3349

    CAS  Google Scholar 

  280. Acharya AN, Ostresh JM, Houghten RA (2001) Tetrahedron 57:9911

    CAS  Google Scholar 

  281. Acharya AN, Ostresh JM, Houghten RA (2001) J Org Chem 66:8673

    CAS  Google Scholar 

  282. Nefzi A, Giulianotti MA, Houghten RA (2001) J Comb Chem 3:68

    CAS  Google Scholar 

  283. Nefzi A, Giulianotti M, Truong L, Rattan S, Ostresh JM, Houghten RA (2002) J Comb Chem 4:175

    CAS  Google Scholar 

  284. Nefzi A, Mimna RA, Houghten RA (2002) J Comb Chem 4:542

    CAS  Google Scholar 

  285. Yu YP, Ostresh JM, Houghten RA (2001) J Comb Chem 3:521

    CAS  Google Scholar 

  286. Yu Y, Ostresh JM, Houghten RA (2003) Biopolymers 71:307

    Google Scholar 

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Authors and Affiliations

  1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms Universität Bonn, Gerhard-Domagk Str. 1, 53121, Bonn, Germany

    Frank Hahn & Ute Schepers

  2. LIMES Institute, Membrane Biology and Lipid Biochemistry, Rheinische Friedrich-Wilhelms Universität Bonn, Gerhard-Domagk Str. 1, 53121, Bonn, Germany

    Frank Hahn & Ute Schepers

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  1. Frank Hahn
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Stefan Bräse

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Hahn, F., Schepers, U. (2007). Solid Phase Chemistry for the Directed Synthesis of Biologically Active Polyamine Analogs, Derivatives, and Conjugates. In: Bräse, S. (eds) Combinatorial Chemistry on Solid Supports. Topics in Current Chemistry, vol 278. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_135

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