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Total (Bio)Synthesis: Strategies of Nature and of Chemists

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Natural Products via Enzymatic Reactions

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 297))

Abstract

The biosynthetic pathways to a number of natural products have been reconstituted in vitro using purified enzymes. Many of these molecules have also been synthesized by organic chemists. Here we compare the strategies used by nature and by chemists to reveal the underlying logic and success of each total synthetic approach for some exemplary molecules with diverse biosynthetic origins.

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References

  1. Nicolaou KC, Vourloumis D, Winssinger N, Baran PS (2000) Angew Chem Int Ed 39:44–122

    CAS  Google Scholar 

  2. Gaudêncio SP, Santos MMM, Lobo AM, Prabhakar S (2003) Tetrahedron Lett 44:2577–2578

    Google Scholar 

  3. Mahboobi S, Eibler E, Koller M, Kumar S, Popp A, Schollmeyer D (1999) J Org Chem 64:4697–4704

    CAS  Google Scholar 

  4. Beccalli EM, Gelmi ML, Marchesini A (1998) Tetrahedron 54:6909–6918

    CAS  Google Scholar 

  5. Wood JL, Stoltz BM, Dietrich HJ (1995) J Am Chem Soc 117:10413–10414

    CAS  Google Scholar 

  6. Xie J, Lown JW (1994) Tetrahedron Lett 35:5555–5558

    CAS  Google Scholar 

  7. Harris W, Hill CH, Keech E, Malsher P (1993) Tetrahedron Lett 34:8361–8364

    Google Scholar 

  8. Faul MM, Sullivan KA, Winneroski LL (1995) Synthesis 1511–1516

    Google Scholar 

  9. Faul MM, Winneroski LL, Krumrich CA (1998) J Org Chem 63:6053–6058

    CAS  Google Scholar 

  10. Moody CJ, Rahimtoola KF, Porter B, Ross BC (1992) J Org Chem 57:2105–2114

    CAS  Google Scholar 

  11. Fabre S, Prudhomme M, Rapp M (1992) Bioorg Med Chem Lett 2:449–452

    CAS  Google Scholar 

  12. Toullec D, Pianetti P, Coste H, Bellevergue P, Grand-Perret T, Ajakane M, Baudet V, Boissin P, Boursier E, Loriolle F et al (1991) J Biol Chem 266:15771–15781

    CAS  Google Scholar 

  13. Hughes I, Nolan WP, Raphael RA (1990) J Chem Soc Perkin Trans I 2475–2480

    Google Scholar 

  14. Sarstedt B, Winterfeldt E (1983) Heterocycles 20:469–476

    CAS  Google Scholar 

  15. Dewick PM (2001) Medicinal natural products – a biosynthetic approach, 3rd edn. Wiley, West Sussex

    Google Scholar 

  16. Davis EM, Croteau R (2000) Top Curr Chem 209:53–95

    CAS  Google Scholar 

  17. Sattely ES, Fischbach MA, Walsh CT (2008) Nat Prod Rep 25:757–793

    CAS  Google Scholar 

  18. Kirby J, Keasling JD (2009) Annu Rev Plant Biol 60:335–355

    CAS  Google Scholar 

  19. Whitehead IM, Threlfall DR, Ewing DF (1989) Phytochemistry 28:775–779

    CAS  Google Scholar 

  20. Takahashi S, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J (2005) J Biol Chem 280:3686–3696

    CAS  Google Scholar 

  21. O'Maille PE; Chappell J; Noel JP (2004) Anal Biochem 335:210–217

    Google Scholar 

  22. Faraldos JA, Zhao Y, O'Maille PE, Noel JP, Coates RM (2007) Chembiochem 8:1826–1833

    CAS  Google Scholar 

  23. Back K, Chappell J (1995) J Biol Chem 270:7375–7381

    CAS  Google Scholar 

  24. Starks CM, Back K, Chappell J, Noel JP (1997) Science 277:1815–1820

    CAS  Google Scholar 

  25. Greenhagen BT, O'Maille PE, Noel JP, Chappell J (2006) Proc Natl Acad Sci USA 103:9826–9831

    Google Scholar 

  26. O'Maille PE, Malone A, Dellas N, Andes Hess B Jr, Smentek L, Sheehan I, Greenhagen BT, Chappell J, Manning G, Noel JP (2008) Nat Chem Biol 4:617–623

    Google Scholar 

  27. Whitehead IM, Ewing DF, Threlfall DR, Cane DE, Prabhakaran PC (1990) Phytochemistry 29:479–482

    CAS  Google Scholar 

  28. Whitehead IM, Threlfall DR, Ewing DF (1987) Phytochemistry 26:1367–1369

    CAS  Google Scholar 

  29. Yoshizawa Y, Yamaura T, Kawaii S, Hoshino T, Mizutani J (1994) Biosci Biotechnol Biochem 58:305–308

    CAS  Google Scholar 

  30. Blay G, Cardona L, Collado AM, García B, Morcillo V, Pedro JR (2004) J Org Chem 69:7294–7302

    CAS  Google Scholar 

  31. Birladeanu L (2003) Angew Chem Int Ed 42:1202–1208

    CAS  Google Scholar 

  32. Hwu JR, Wetzel JM (1992) J Org Chem 57:922–928

    CAS  Google Scholar 

  33. Neilands JB (1981) Annu Rev Nutr 1:27–46

    CAS  Google Scholar 

  34. Neilands JB (1981) Annu Rev Biochem 50:715–731

    CAS  Google Scholar 

  35. Butler A (1998) Science 281:207–209

    CAS  Google Scholar 

  36. Wake A, Misawa M, Matsui A (1975) Infect Immun 12:1211–1213

    Google Scholar 

  37. Haag H, Hantke K, Drechsel H, Stojiljkovic I, Jung G, Zahner H (1993) J Gen Microbiol 139:2159–2165

    CAS  Google Scholar 

  38. Drechsel H, Stephan H, Lotz R, Haag H, Zähner H, Hantke K, Jung G (1995) Liebigs Ann 1995:1727–1733

    Google Scholar 

  39. Miller MC, Parkin S, Fetherston JD, Perry RD, DeMoll E (2006) J Inorg Biochem 100:1495–1500

    CAS  Google Scholar 

  40. Perry RD, Fetherston JD (1997) Clin Microbiol Rev 10:35–66

    CAS  Google Scholar 

  41. Buchrieser C, Brosch R, Bach S, Guiyoule A, Carniel E (1998) Mol Microbiol 30:965–978

    CAS  Google Scholar 

  42. Chambers CE, McIntyre DD, Mouck M, Sokol PA (1996) Biometals 9:157–167

    CAS  Google Scholar 

  43. Valdebenito M, Bister B, Reissbrodt R, Hantke K, Winkelmann G (2005) Int J Med Microbiol 295:99–107

    CAS  Google Scholar 

  44. Henderson JP, Crowley JR, Pinkner JS, Walker JN, Tsukayama P, Stamm WE, Hooton TM, Hultgren SJ (2009) PLoS Pathog 5:e1000305

    Google Scholar 

  45. Bultreys A, Gheysen I, de Hoffmann E (2006) Appl Environ Microbiol 72:3814–3825

    CAS  Google Scholar 

  46. Perry RD, Balbo PB, Jones HA, Fetherston JD, DeMoll E (1999) Microbiology 145:1181–1190

    CAS  Google Scholar 

  47. Heesemann J (1987) FEMS Microbiol Lett 48:229–233

    CAS  Google Scholar 

  48. Bearden SW, Perry RD (1999) Mol Microbiol 32:403–414

    CAS  Google Scholar 

  49. Rakin A, Saken E, Harmsen D, Heesemann J (1994) Mol Microbiol 13:253–263

    CAS  Google Scholar 

  50. Ferreras JA, Ryu J-S, Di Lello F, Tan DS, Quadri LEN (2005) Nat Chem Biol 1:29–32

    CAS  Google Scholar 

  51. Stirrett KL, Ferreras JA, Jayaprakash V, Sinha BN, Ren T, Quadri LEN (2008) Bioorg Med Chem Lett 18:2662–2668

    CAS  Google Scholar 

  52. Bearden S, Fetherston J, Perry R (1997) Infect Immun 65:1659–1668

    CAS  Google Scholar 

  53. Pelludat C, Rakin A, Jacobi CA, Schubert S, Heesemann J (1998) J Bacteriol 180:538–546

    CAS  Google Scholar 

  54. Gehring AM, DeMoll E, Fetherston JD, Mori I, Mayhew GF, Blattner FR, Walsh CT, Perry RD (1998) Chem Biol 5:573–586

    CAS  Google Scholar 

  55. Fetherston JD, Bearden SW, Perry RD (1996) Mol Microbiol 22:315–325

    CAS  Google Scholar 

  56. Anisimov R, Brem D, Heesemann J, Rakin A (2005) Int J Med Microbiol 295:19–28

    CAS  Google Scholar 

  57. Brem D, Pelludat C, Rakin A, Jacobi CA, Heesemann J (2001) Microbiology 147:1115–1127

    CAS  Google Scholar 

  58. Fetherston JD, Bertolino VJ, Perry RD (1999) Mol Microbiol 32:289–299

    CAS  Google Scholar 

  59. Schubert S, Rakin A, Heesemen J (2004) Int J Med Microbiol 294:83–94

    CAS  Google Scholar 

  60. Buchrieser C, Rusniok C, Frangeul L, Couve E, Billault A, Kunst F, Carniel E, Glaser P (1999) Infect Immun 67:4851–4861

    CAS  Google Scholar 

  61. Antonenka U, Nölting C, Heesemann J, Rakin A (2005) Mol Microbiol 57:727–734

    CAS  Google Scholar 

  62. Miller DA, Luo L, Hillson N, Keating TA, Walsh CT (2002) Chem Biol 9:333–344

    CAS  Google Scholar 

  63. Pelludat C, Brem D, Heesemann J (2003) J Bacteriol 185:5648–5653

    CAS  Google Scholar 

  64. Kerbarh O, Ciulli A, Howard NI, Abell C (2005) J Bacteriol 187:5061–5066

    CAS  Google Scholar 

  65. Patel HM, Tao J, Walsh CT (2003) Biochemistry 42:10514–10527

    CAS  Google Scholar 

  66. Bobrov AG, Geoffroy VA, Perry RD (2002) Infect Immun 70:4204–4214

    CAS  Google Scholar 

  67. Geoffroy VA, Fetherston JD, Perry RD (2000) Infect Immun 68:4452–4461

    CAS  Google Scholar 

  68. Patel HM, Walsh CT (2001) Biochemistry 40:9023–9031

    CAS  Google Scholar 

  69. Darling P, Chan M, Cox AD, Sokol PA (1998) Infect Immun 66:874–877

    CAS  Google Scholar 

  70. Cox CD (1980) J Bacteriol 142:581–587

    CAS  Google Scholar 

  71. Liu PV, Shokrani F (1978) Infect Immun 22:878–890

    CAS  Google Scholar 

  72. Cox CD, Rinehart KLJ, Moore ML, Cook JC Jr (1981) Proc Natl Acad Sci USA 78:4256–4260

    CAS  Google Scholar 

  73. Cobessi D, Celia H, Pattus F (2005) J Mol Biol 352:893–904

    CAS  Google Scholar 

  74. Tseng C-F, Burger A, Mislin G, Schalk I, Yu S, Chan S, Abdallah M (2006) J Biol Inorg Chem 11:419–432

    CAS  Google Scholar 

  75. Reimmann C, Patel HM, Serino L, Barone M, Walsh CT, Haas D (2001) J Bacteriol 183:813–820

    CAS  Google Scholar 

  76. Ino A, Murabayashi A (2001) Tetrahedron 57:1897–1902

    CAS  Google Scholar 

  77. Ino A, Hasegawa Y, Murabayashi A (1998) Tetrahedron Lett 39:3509–3512

    CAS  Google Scholar 

  78. Kemp DS, Carey RI (2002) J Org Chem 54:3640–3646

    Google Scholar 

  79. Ankenbauer RG, Toyokuni T, Staley A, Rinehart KL Jr, Cox CD (1988) J Bacteriol 170:5344–5351

    CAS  Google Scholar 

  80. Rinehart KL, Staley AL, Wilson SR, Ankenbauer RG, Cox CD (1995) J Org Chem 60:2786–2791

    CAS  Google Scholar 

  81. Rivault F, Schons V, Liébert C, Burger A, Sakr E, Abdallah MA, Schalk IJ, Mislin GLA (2006) Tetrahedron 62:2247–2254

    CAS  Google Scholar 

  82. Zamri A, Abdallah MA (2000) Tetrahedron 56:249–256

    CAS  Google Scholar 

  83. Pollack JR, Neilands JB (1970) Biochem Biophys Res Commun 38:989–992

    CAS  Google Scholar 

  84. O'Brien I, Gibson F (1970) Biochim Biophys Acta 215:393–402

    Google Scholar 

  85. Shanzer A, Libman J, Lifson S, Felder CE (1986) J Am Chem Soc 108:7609–7619

    CAS  Google Scholar 

  86. Carrano CJ, Raymond KN (1979) J Am Chem Soc 101:5401–5404

    CAS  Google Scholar 

  87. Harris WR, Carrano CJ, Cooper SR, Sofen SR, Avdeef AE, McArdle JV, Raymond KN (1979) J Am Chem Soc 101:6097–6104

    CAS  Google Scholar 

  88. Konopka K, Neilands JB (1984) Biochemistry 23:2122–2127

    CAS  Google Scholar 

  89. Goetz DH, Holmes MA, Borregaard N, Bluhm ME, Raymond KN, Strong RK (2002) Mol Cell 10:1033–1043

    CAS  Google Scholar 

  90. Holmes MA, Paulsene W, Jide X, Ratledge C, Strong RK (2005) Stucture 13:29–41

    CAS  Google Scholar 

  91. Bister B, Bischoff D, Nicholson GJ, Valdebenito M, Schneider K, Winkelmann G, Hantke K, Süssmuth RD (2004) Biometals 17:471–481

    CAS  Google Scholar 

  92. Hantke K, Nicholson G, Rabsch W, Winkelmann G (2003) Proc Natl Acad Sci USA 100:3677–3682

    CAS  Google Scholar 

  93. Fischbach MA, Lin H, Liu DR, Walsh CT (2006) Nat Chem Biol 2:132–138

    CAS  Google Scholar 

  94. Luo M, Lin H, Fischbach MA, Liu DR, Walsh CT, Groves JT (2006) ACS Chem Biol 1:29–32

    CAS  Google Scholar 

  95. Fischbach MA, Lin H, Zhou L, Yu Y, Abergel RJ, Liu DR, Raymond KN, Wanner BL, Strong RK, Walsh CT, Aderem A, Smith KD (2006) Proc Natl Acad Sci USA 103:16502–16507

    CAS  Google Scholar 

  96. de Lorenzo V (1984) Arch Microbiol 139:72–75

    Google Scholar 

  97. Lagos R, Wilkens M, Vergara C, Cecchi X, Monasterio O (1993) FEBS Lett 321:145–148

    CAS  Google Scholar 

  98. Thomas X, Destoumieux-Garzón D, Peduzzi J, Afonso C, Blond A, Birlirakis N, Goulard C, Dubost L, Thai R, Tabet J-C, Rebuffat S (2004) J Biol Chem 279:28233–28242

    CAS  Google Scholar 

  99. Nolan EM, Fischbach MA, Koglin A, Walsh CT (2007) J Am Chem Soc 129:14336–14347

    CAS  Google Scholar 

  100. Vassiliadis G, Peduzzi J, Zirah S, Thomas X, Rebuffat S, Destoumieux-Garzon D (2007) Antimicrob Agents Chemother 51:3546–3553

    CAS  Google Scholar 

  101. Kaiser A, Leistner E (1990) Arch Biochem Biophys 276:331–335

    CAS  Google Scholar 

  102. Liu J, Quinn N, Berchtold GA, Walsh CT (1990) Biochemistry 29:1417–1425

    CAS  Google Scholar 

  103. Tummuru MK, Brickman TJ, McIntosh MA (1989) J Biol Chem 264:20547–20551

    CAS  Google Scholar 

  104. Gehring AM, Bradley KA, Walsh CT (1997) Biochemistry 36:8495–8503

    CAS  Google Scholar 

  105. Rusnak F, Liu J, Quinn N, Berchtold GA, Walsh CT (1990) Biochemistry 29:1425–1435

    CAS  Google Scholar 

  106. Liu J, Duncan K, Walsh CT (1989) J Bacteriol 171:791–798

    Google Scholar 

  107. Gehring AM, Mori I, Walsh CT (1998) Biochemistry 37:2648–2659

    CAS  Google Scholar 

  108. Shaw-Reid CA, Kelleher NL, Losey HC, Gehring AM, Berg C, Walsh CT (1999) Chem Biol 6:385–400

    CAS  Google Scholar 

  109. Fischbach MA, Lin H, Liu DR, Walsh CT (2005) Proc Natl Acad Sci USA 102:571–576

    CAS  Google Scholar 

  110. Zhu M, Valdebenito M, Winkelmann G, Hantke K (2005) Microbiology 151:2363–2372

    CAS  Google Scholar 

  111. Lin H, Fischbach MA, Liu DR, Walsh CT (2005) J Am Chem Soc 127:11075–11084

    CAS  Google Scholar 

  112. Lagos R, Villanueva JE, Monasterio O (1999) J Bacteriol 181:212–217

    CAS  Google Scholar 

  113. Corey EJ, Bhattacharyya S (1977) Tetrahedron Lett 45:3919–3922

    Google Scholar 

  114. Rastetter WH, Erickson TJ, Venuti MC (1980) J Org Chem 45:5011–5012

    CAS  Google Scholar 

  115. Rogers HJ (1995) J Chem Soc Perkin Trans I 3073–3075

    Google Scholar 

  116. Shanzer A, Libman J (1983) J Chem Soc Chem Commun 846–847

    Google Scholar 

  117. Marinez ER, Salmassian EK, Lau TT, Gutierrez CG (1996) J Org Chem 61:3548–3550

    CAS  Google Scholar 

  118. Meyer M, Telford JR, Cohen SM, White DJ, Xu J, Raymond KN (1997) J Am Chem Soc 119:10093–10103

    CAS  Google Scholar 

  119. Ramirez RJA, Karamanukyan L, Ortiz S, Gutierrez CG (1997) Tetrahedron Lett 38:749–752

    CAS  Google Scholar 

  120. Rastetter WH, Erickson TJ, Venuti MC (1981) J Org Chem 46:3579–3590

    CAS  Google Scholar 

  121. Gong H, Gagné MR (2008) J Am Chem Soc 130:12177–12183

    CAS  Google Scholar 

  122. Silakowski B, Kunze B, Nordsiek G, Blöcker H, Höfle G, Müller R (2000) Eur. J Biochem 267:6476–6485

    CAS  Google Scholar 

  123. Miyanaga S, Obata T, Onaka H, Fujita T, Saito N, Sakurai H, Saiki I, Furumai T, Igarashi Y (2006) J Antibiot (Tokyo) 59:698–703

    CAS  Google Scholar 

  124. Keating TA, Marshall CG, Walsh CT (2000) Biochemistry 39:15522–15530

    CAS  Google Scholar 

  125. Gaitatzis N, Kunze B, Müller R (2001) Proc Natl Acad Sci USA 98:11136–11141

    CAS  Google Scholar 

  126. Silakowski B, Schairer HU, Ehret H, Kunze B, Weinig S, Nordsiek G, Brandt P, Blöcker H, Höfle G, Beyer S, Müller R (1999) J Biol Chem 274:37391–37399

    CAS  Google Scholar 

  127. Griffiths GL, Sigel SP, Payne SM, Neilands JB (1984) J Biol Chem 259:383–385

    CAS  Google Scholar 

  128. Keating TA, Marshall CG, Walsh CT (2000) Biochemistry 39:15513–15521

    CAS  Google Scholar 

  129. Butterton JR, Choi MH, Watnick PI, Carroll PA, Calderwood SB (2000) J Bacteriol 182:1731–1738

    CAS  Google Scholar 

  130. Zhou Z, Lai JR, Walsh CT (2007) Proc Natl Acad Sci USA 104:11621–11626

    CAS  Google Scholar 

  131. Bergeron RJ, Garlich JR, McManis JS (1985) Tetrahedron 41:507–510

    CAS  Google Scholar 

  132. Sakakura A, Umemura S, Ishihara K (2008) Chem Commun 3561–3563

    Google Scholar 

  133. Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya J, Tsuchiya H, Takahashi Y, Masuma R (1977) J Antibiot (Tokyo) 30:275–282

    CAS  Google Scholar 

  134. Xie Q, Wang Y, Huang Y, Wu Y, Ba F, Liu Z (2002) Int J Syst Evol Microbiol 52:1815–1820

    CAS  Google Scholar 

  135. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F (1986) Biochem Biophys Res Commun 135:397–402

    CAS  Google Scholar 

  136. Hoehn P, Ghisalba O, Moerker T, Peter HH (1995) J Antibiot (Tokyo) 48:300–305

    CAS  Google Scholar 

  137. Takahashi I, Kobayashi E, Asano K, Yoshida M, Nakano H (1987) J Antibiot (Tokyo) 40:1782–1784

    CAS  Google Scholar 

  138. Lapenna S, Giordano A (2009) Nat Rev Drug Discov 8:547–566

    CAS  Google Scholar 

  139. Akinaga S, Sugiyama K, Akiyama T (2000) Anticancer Drug Des 15:43–52

    CAS  Google Scholar 

  140. Link JT, Raghavan S, Danishefsky SJ (1995) J Am Chem Soc 117:552–553

    CAS  Google Scholar 

  141. Link JT, Raghavan S, Gallant M, Danishefsky SJ, Chou TC, Ballas LM (1996) J Am Chem Soc 118:2825–2842

    CAS  Google Scholar 

  142. Wood JL, Stoltz BM, Goodman SN (1996) J Am Chem Soc 118:10656–10657

    CAS  Google Scholar 

  143. Wood JL, Stoltz BM, Goodman SN, Onwneme K (1997) J Am Chem Soc 119:9652–9661

    CAS  Google Scholar 

  144. Onaka H, Taniguchi S, Igarashi Y, Furumai T (2002) J Antibiot (Tokyo) 55:1063–1071

    CAS  Google Scholar 

  145. Kim SY, Park JS, Chae CS, Hyun CG, Choi BW, Shin J, Oh KB (2007) Appl Microbiol Biotechnol 75:1119–1126

    CAS  Google Scholar 

  146. Gao Q, Zhang C, Blanchard S, Thorson JS (2006) Chem Biol 13:733–743

    CAS  Google Scholar 

  147. Sánchez C, Butovich IA, Braña AF, Rohr J, Méndez C, Salas JA (2002) Chem Biol 9:519–531

    Google Scholar 

  148. Onaka H, Taniguchi S, Igarashi Y, Furumai T (2003) Biosci Biotechnol Biochem 67:127–138

    CAS  Google Scholar 

  149. Balibar CJ, Walsh CT (2006) Biochemistry 45:15444–15457

    CAS  Google Scholar 

  150. Sánchez C, Zhu L, Braña AF, Salas AP, Rohr J, Méndez C, Salas JA (2005) Proc Natl Acad Sci USA 102:461–466

    Google Scholar 

  151. Nishizawa T, Aldrich CC, Sherman DH (2005) J Bacteriol 187:2084–2092

    CAS  Google Scholar 

  152. Howard-Jones AR, Walsh CT (2005) Biochemistry 44:15652–15663

    CAS  Google Scholar 

  153. Howard-Jones AR, Walsh CT (2006) J Am Chem Soc 128:12289–12298

    CAS  Google Scholar 

  154. Ryan KS, Howard-Jones AR, Hamill MJ, Elliott SJ, Walsh CT, Drennan CL (2007) Proc Natl Acad Sci USA 104:15311–15316

    CAS  Google Scholar 

  155. Nishizawa T, Gruschow S, Jayamaha DH, Nishizawa-Harada C, Sherman DH (2006) J Am Chem Soc 128:724–725

    CAS  Google Scholar 

  156. Wang Y, Chen H, Makino M, Shiro Y, Nagano S, Asamizu S, Onaka H, Shaik S (2009) J Am Chem Soc 131:6748–6762

    CAS  Google Scholar 

  157. Makino M, Sugimoto H, Shiro Y, Asamizu S, Onaka H, Nagano S (2007) Proc Natl Acad Sci USA 104:11591–11596

    CAS  Google Scholar 

  158. Asamizu S, Kato Y, Igarashi Y, Furumai T, Onaka H (2006) Tetrahedron Lett 47:473–475

    CAS  Google Scholar 

  159. Sánchez C, Braña AF, Méndez C, Salas JA (2006) Chembiochem 7:1231–1240

    Google Scholar 

  160. Salas AP, Zhu L, Sánchez C, Braña AF, Rohr J, Méndez C, Salas JA (2005) Mol Microbiol 58:17–27

    CAS  Google Scholar 

  161. Sánchez C, Salas AP, Braña AF, Palomino M, Pineda-Lucena A, Carbajo RJ, Méndez C, Moris F, Salas JA (2009) Chem Commun 4118–4120

    Google Scholar 

  162. Nakanishi S, Matsuda Y, Iwahashi K, Kase H (1986) J Antibiot (Tokyo) 39:1066–1071

    CAS  Google Scholar 

  163. Ryan KS, Drennan CL (2009) Chem Biol 16:351–364

    CAS  Google Scholar 

  164. Sánchez C, Méndez C, Salas JA (2006) Nat Prod Rep 23:1007–1045

    Google Scholar 

  165. Chae CS, Park JS, Chung SC, Kim TI, Lee SH, Yoon KM, Shin J, Oh KB (2009) Bioorg Med Chem Lett 19:1581–1583

    CAS  Google Scholar 

  166. Penn K, Jenkins C, Nett M, Udwary DW, Gontang EA, McGlinchey RP, Foster B, Lapidus A, Podell S, Allen EE, Moore BS, Jensen PR (2009) ISME J 3:1193–1203

    Google Scholar 

  167. Howard-Jones AR, Walsh CT (2007) J Am Chem Soc 129:11016–11017

    CAS  Google Scholar 

  168. Mentel M, Ahuja EG, Mavrodi DV, Breinbauer R, Thomashow LS, Blankenfeldt W (2009) Chembiochem 10:2295–2304

    CAS  Google Scholar 

  169. Hassan HM, Fridovich I (1980) J Bacteriol 141:156–163

    Google Scholar 

  170. Lau GW, Ran H, Kong F, Hassett DJ, Mavrodi D (2004) Infect Immun 72:4275–4278

    CAS  Google Scholar 

  171. Ran H, Hassett DJ, Lau GW (2003) Proc Natl Acad Sci USA 100:14315–14320

    CAS  Google Scholar 

  172. Allen L, Dockrell DH, Pattery T, Lee DG, Cornelis P, Hellewell PG, Whyte MK (2005) J Immunol 174:3643–3649

    CAS  Google Scholar 

  173. Bianchi SM, Prince LR, McPhillips K, Allen L, Marriott HM, Taylor GW, Hellewell PG, Sabroe I, Dockrell DH, Henson PW, Whyte MK (2008) Am J Respir Crit Care Med 177:35–43

    CAS  Google Scholar 

  174. Look DC, Stoll LL, Romig SA, Humlicek A, Britigan BE, Denning GM (2005) J Immunol 175:4017–4023

    CAS  Google Scholar 

  175. Price-Whelan A, Dietrich LE, Newman DK (2007) J Bacteriol 189:6372–6381

    Google Scholar 

  176. Hernandez ME, Kappler A, Newman DK (2004) Appl Environ Microbiol 70:921–928

    CAS  Google Scholar 

  177. Dietrich LE, Price-Whelan A, Petersen A, Whiteley M, Newman DK (2006) Mol Microbiol 61:1308–1321

    CAS  Google Scholar 

  178. Dietrich LE, Teal TK, Price-Whelan A, Newman DK (2008) Science 321:1203–1206

    CAS  Google Scholar 

  179. Deppenmeier U, Johann A, Hartsch T, Merkl R, Schmitz RA, Martinez-Arias R, Henne A, Wiezer A, Baumer S, Jacobi C, Bruggemann H, Lienard T, Christmann A, Bomeke M, Steckel S, Bhattacharyya A, Lykidis A, Overbeek R, Klenk HP, Gunsalus RP, Fritz HJ, Gottschalk G (2002) J Mol Microbiol Biotechnol 4:453–461

    CAS  Google Scholar 

  180. Millican RC (1962) Biochem Biophys Acta 57:407–409

    CAS  Google Scholar 

  181. Mavrodi DV, Ksenzenko VN, Bonsall RF, Cook RJ, Boronin AM, Thomashow LS (1998) J Bacteriol 180:2541–2548

    CAS  Google Scholar 

  182. Pierson LS III, Gaffney T, Lam S, Gong F (1995) FEMS Microbiol Lett 134:299–307

    Google Scholar 

  183. Mavrodi DV, Bonsall RF, Delaney SM, Soule MJ, Phillips G, Thomashow LS (2001) J Bacteriol 183:6454–6465

    CAS  Google Scholar 

  184. Giddens SR, Feng Y, Mahanty HK (2002) Mol Microbiol 45:769–783

    CAS  Google Scholar 

  185. Haagen Y, Gluck K, Fay K, Kammerer B, Gust B, Heide L (2006) Chembiochem 7:2016–2027

    CAS  Google Scholar 

  186. Saleh O, Gust B, Boll B, Fiedler HP, Heide L (2009) J Biol Chem 284:14439–14447

    CAS  Google Scholar 

  187. Olekhovich IN, Kotik EA, Formichev YK (1994) Genetika 30:285–286

    CAS  Google Scholar 

  188. McDonald M, Mavrodi DV, Thomashow LS, Floss HG (2001) J Am Chem Soc 123:9459–9460

    CAS  Google Scholar 

  189. Parsons JF, Calabrese K, Eisenstein E, Ladner JE (2003) Biochemistry 42:5684–5693

    CAS  Google Scholar 

  190. Blankenfeldt W, Kuzin AP, Skarina T, Korniyenko Y, Tong L, Bayer P, Janning P, Thomashow LS, Mavrodi DV (2004) Proc Natl Acad Sci USA 101:16431–16436

    CAS  Google Scholar 

  191. Parsons JF, Calabrese K, Eisenstein E, Ladner JE (2004) Acta Crystallogr D Biol Crystallogr 60:2110–2113

    Google Scholar 

  192. Parsons JF, Song F, Parsons L, Calabrese K, Eisenstein E, Ladner JE (2004) Biochemistry 43:12427–12435

    CAS  Google Scholar 

  193. Ahuja EG, Janning P, Mentel M, Graebsch A, Breinbauer R, Hiller W, Costisella B, Thomashow LS, Mavrodi DV, Blankenfeldt W (2008) J Am Chem Soc 130:17053–17061

    CAS  Google Scholar 

  194. Parsons JF, Greenhagen BT, Shi K, Calabrese K, Robinson H, Ladner JE (2007) Biochemistry 46:1821–1828

    CAS  Google Scholar 

  195. Greenhagen BT, Shi K, Robinson H, Gamage S, Bera AK, Ladner JE, Parsons JF (2008) Biochemistry 47:5281–5289

    CAS  Google Scholar 

  196. Müller PK, Krohn K, Mühlradt PF (1989) Infect Immun 57:2591–2596

    Google Scholar 

  197. Surrey AR (1967) Pyocyanine. In: Horning EC (ed) Organic syntheses collection, vol 3. Wiley, New York, pp 753–756

    Google Scholar 

  198. Sitachitta N, Gadepalli M, Davidson BS (1996) Tetrahedron 52:8073–8080

    CAS  Google Scholar 

  199. Miyairi N, Sakai H-I, Konomi T, Imanaka H (1976) J Antibiot (Tokyo) 29:227–235

    CAS  Google Scholar 

  200. Tokuma Y, Miyairi N, Morimoto Y (1976) J Antibiot (Tokyo) 29:1114–1116

    CAS  Google Scholar 

  201. Seto H, Sato T, Urano S, Uzawa J, Yonehara H (1976) Tetrahedron Lett 17:4367–4370

    Google Scholar 

  202. Kang H, Jensen PR, Fenical W (1996) J Org Chem 61:1543–1546

    CAS  Google Scholar 

  203. Zhang H-I, He X-g, Adefarati A, Gallucci J, Cole SP, Beale JM, Keller PJ, Chang C-j, Floss HG (1990) J Org Chem 55:1682–1684

    Google Scholar 

  204. Hertweck C, Luzhetskyy A, Rebets Y, Bechthold A (2007) Nat Prod Rep 24:162–190

    CAS  Google Scholar 

  205. Hertweck C (2009) Angew Chem Int Ed 48:4688–4716

    CAS  Google Scholar 

  206. Piel J, Hoang K, Moore BS (2000) J Am Chem Soc 122:5415–5416

    CAS  Google Scholar 

  207. Piel J, Hertweck C, Shipley PR, Hunt DM, Newman MS, Moore BS (2000) Chem Biol 7:943–955

    CAS  Google Scholar 

  208. Hertweck C, Moore BS (2000) Tetrahedron 56:9115–9120

    CAS  Google Scholar 

  209. Xiang L, Moore BS (2003) J Bacteriol 185:399–404

    CAS  Google Scholar 

  210. Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ (2001) Chembiochem 10:784–786

    Google Scholar 

  211. Xiang L, Moore BS (2002) J Biol Chem 277:32505–32509

    CAS  Google Scholar 

  212. Izumikawa M, Cheng Q, Moore BS (2006) J Am Chem Soc 128:1428–1429

    CAS  Google Scholar 

  213. Hertweck C, Xiang L, Kalaitzis JA, Cheng Q, Palzer M, Moore BS (2004) Chem Biol 11:461–468

    CAS  Google Scholar 

  214. Xiang L, Kalaitzis JA, Moore BS (2004) Proc Natl Acad Sci USA 101:15609–15614

    CAS  Google Scholar 

  215. Cheng Q, Xiang L, Izumikawa M, Meluzzi D, Moore BS (2007) Nat Chem Biol 3:557–558

    CAS  Google Scholar 

  216. Florova G, Kazanina G, Reynolds KA (2002) Biochemistry 41:10462–10471

    CAS  Google Scholar 

  217. Xiang L, Kalaitzis JA, Nilsen G, Chen L, Moore BS (2002) Org Lett 4:957–960

    CAS  Google Scholar 

  218. Caro AA, Cederbaum AI (2005) Biochem Pharmacol 69:1081–1093

    CAS  Google Scholar 

  219. Pohl NL, Hans M, Lee HY, Kim YS, Cane DE, Khosla C (2001) J Am Chem Soc 123:5822–5823

    CAS  Google Scholar 

  220. Kalaitzis JA, Cheng Q, Thomas PM, Kelleher NL, Moore BS (2009) J Nat Prod 72:469–472

    CAS  Google Scholar 

  221. Kalaitzis JA, Izumikawa M, Xiang L, Hertweck C, Moore BS (2003) J Am Chem Soc 125:9290–9291

    CAS  Google Scholar 

  222. Kirsch S, Bach T (2003) Angew Chem Int Ed 42:4685–4687

    CAS  Google Scholar 

  223. Kirsch SF, Bach T (2005) Chem Eur J 11:7007–7023

    CAS  Google Scholar 

  224. Hatakeyama S, Numata H, Osanai K, Takano S (1989) J Org Chem 54:3515–3517

    CAS  Google Scholar 

  225. Young IS, Baran PS (2009) Nat Chem 1:193–205

    CAS  Google Scholar 

  226. Baran PS, Maimone TJ, Richter JM (2007) Nature 446:404–408

    CAS  Google Scholar 

  227. Roethle PA, Hernandez PT, Trauner D (2006) Org Lett 8:5901–5904

    CAS  Google Scholar 

  228. Roethle PA, Trauner D (2006) Org Lett 8:345–347

    CAS  Google Scholar 

  229. Chen K, Baran PS (2009) Nature 459:824–828

    CAS  Google Scholar 

  230. Chen MS, White MC (2007) Science 318:783–787

    CAS  Google Scholar 

  231. Zhan J, Guo H, Dai J, Zhang Y, Guo D (2002) Tetrahedron Lett 43:4519–4521

    CAS  Google Scholar 

  232. Nicolaou KC, Montagnon T, Snyder SA (2003) Chem Commun 551–564

    Google Scholar 

  233. Nicolaou KC, Edmonds DJ, Bulger PG (2006) Angew Chem Int Ed 45:7134–7186

    CAS  Google Scholar 

  234. Nicolaou KC, Chen JS (2009) Chem Soc Rev 38:2993–3009

    CAS  Google Scholar 

  235. Johnson WS, Gravenstock MB, McCarry BE (1971) J Am Chem Soc 93:4332–4334

    CAS  Google Scholar 

  236. Nicolaou KC, Frederick MO, Aversa RJ (2008) Angew Chem Int Ed 47:7182–7225

    CAS  Google Scholar 

  237. Vilotijevic I, Jamison TF (2009) Angew Chem Int Ed 48:5250–5281

    CAS  Google Scholar 

  238. Tanuwidjaja J, Ng S-S, Jamison TF (2009) J Am Chem Soc 13:12084–12085

    Google Scholar 

  239. Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Stuermer R, Zelinski T (2004) Angew Chem Int Ed 43:788–824

    CAS  Google Scholar 

  240. Drauz K, Waldmann H (1995) Enzyme catalysis in organic synthesis. Wiley, Weinheim

    Google Scholar 

  241. Gotor V (2008) Asymmetric organic synthesis with enzymes. Wiley, Weinheim

    Google Scholar 

  242. Werneburg M, Hertweck C (2008) Chembiochem 9:2064–2066

    CAS  Google Scholar 

  243. Richter MEA, Traitcheva N, Knuepfer U, Hertweck C (2008) Angew Chem Int Ed 47:8872–8875

    CAS  Google Scholar 

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Acknowledgments

This work was supported by National Institutes of Health grants GM85770 and AI47818 to B.S.M., a postdoctoral fellowship from the German Academic Exchange Service (DAAD) to T.A.M.G. and a Howard Hughes Medical Institute sponsored Life Sciences Research Foundation postdoctoral fellowship to K.S.R.

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  1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, La Jolla, CA, 92093, USA

    Alexandra A. Roberts, Katherine S. Ryan, Bradley S. Moore & Tobias A. M. Gulder

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  1. Alexandra A. Roberts
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  2. Katherine S. Ryan
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  3. Bradley S. Moore
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  4. Tobias A. M. Gulder
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Correspondence to Bradley S. Moore or Tobias A. M. Gulder .

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

    Jörn Piel

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Roberts, A.A., Ryan, K.S., Moore, B.S., Gulder, T.A.M. (2010). Total (Bio)Synthesis: Strategies of Nature and of Chemists. In: Piel, J. (eds) Natural Products via Enzymatic Reactions. Topics in Current Chemistry, vol 297. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_79

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