Skip to main content

Microbial Isoprenoid Production: An Example of Green Chemistry through Metabolic Engineering

  • Chapter
  • First Online:
Book cover Biotechnology for the Future

Abstract

Saving energy, cost efficiency, producing less waste, improving the biodegradability of products, potential for producing novel and complex molecules with improved properties, and reducing the dependency on fossil fuels as raw materials are the main advantages of using biotechnological processes to produce chemicals. Such processes are often referred to as green chemistry or white biotechnology. Metabolic engineering, which permits the rational design of cell factories using directed genetic modifications, is an indispensable strategy for expanding green chemistry. In this chapter, the benefits of using metabolic engineering approaches for the development of green chemistry are illustrated by the recent advances in microbial production of isoprenoids, a diverse and important group of natural compounds with numerous existing and potential commercial applications. Accumulated knowledge on the metabolic pathways leading to the synthesis of the principal precursors of isoprenoids is reviewed, and recent investigations into isoprenoid production using engineered cell factories are described.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

ATP:

Adenosine triphosphate

CDP-ME:

4-diphosphocytidyl-2C-methyl-D-erythritol

CDP-ME2P:

2-phospho-4-diphosphocytidyl-2C-methyl-D-erythritol

CMP:

Cytidine monophosphate

CTP:

Cytidine triphosphate

CoA:

Coenzyme A

DMAPP:

Dimethylallyl diphosphate

DXP:

1-deoxy-D-xylulose 5-phosphate

ERAD:

Endoplasmic reticulum associated degradation

FOH:

Farnesol

FPP:

Farnesyl diphosphate

GAP:

D-glyceraldehyde 3-phosphate

GGPP:

Geranylgeranyl diphosphate

GMO:

Genetically modified organism

GPP:

Geranyl diphosphate

HMBPP:

1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate

HMG-CoA:

3-hydroxy-3-methylglutaryl coenzyme A

IPP:

Isopentenyl diphosphate

MECDP:

2-C-methyl-D-erythritol 2,4-cyclodiphosphate

MEP:

2-methylerythritol 4-phosphate

MCA:

Metabolic control analysis

MFA:

Metabolic flux analysis

mRNA:

Messenger ribonucleic acid

NADP:

Nicotinamide adenine dinucleotide phosphate

PEP:

Phosphoenolpyruvate

RNA:

Ribonucleic acid

TPP:

Thiamine diphosphate

tRNA:

Transfer ribonucleic acid

References

  1. Nielsen J (2001) Appl Microbiol Biot 55:263

    CAS  Google Scholar 

  2. Ostergaard S, Olsson L, Nielsen J (2001) Biotechnol Bioeng 73:412

    CAS  Google Scholar 

  3. Thykaer J, Nielsen J (2003) Metab Eng 5:56

    CAS  Google Scholar 

  4. Stephanopoulos G, Gill RT (2001) Adv Biochem Eng Biotechnol 73:1

    CAS  Google Scholar 

  5. Burkart MD (2003) Org Biomol Chem 1:1

    CAS  Google Scholar 

  6. Grabley S, Thiericke R (1999) Adv Biochem Eng Biotechnol 64:101

    CAS  Google Scholar 

  7. EuropaBio (2003) White biotechnology: Gateway to a more sustainable future. EuropaBio, Lyon. Available at http://www.mckinsey.com/clientservice/chemicals/pdf/BioVision_Booklet_final.pdf

    Google Scholar 

  8. Robin J, Jakobsen M, Beyer M, Noorman H, Nielsen J (2001) Appl Microbiol Biotechnol 57:357

    CAS  Google Scholar 

  9. Sacchettini JC, Poulter CD (1997) Science 277:1788

    CAS  Google Scholar 

  10. McCaskill D, Croteau R (1997) Adv Biochem Eng Biotechnol 55:107

    CAS  Google Scholar 

  11. Wallach O (1887) Justus Liebigs Ann Chem 239:1

    Google Scholar 

  12. Ruzicka L (1953) Experientia 9:357

    CAS  Google Scholar 

  13. Katsuki H, Bloch K (1967) J Biol Chem 242:222

    CAS  Google Scholar 

  14. Lynen F (1967) Pure Appl Chem 14:137

    CAS  Google Scholar 

  15. Rohmer M, Knani M, Simonin P, Sutter B, Sahm H (1993) Biochem J 295:517

    CAS  Google Scholar 

  16. Rohmer M (1999) Nat Prod Rep 16:565

    CAS  Google Scholar 

  17. Broers STJ (1994) PhD thesis, Eidgenössische Technische Hochschule Zürich

    Google Scholar 

  18. Schwarz MK (1994) PhD thesis, Eidgenössische Technische Hochschule Zürich

    Google Scholar 

  19. Bach TJ, Boronat A, Campos N, Ferrer A, Vollack K-U (1999) Crit Rev Biochem Mol Biol 34:107

    CAS  Google Scholar 

  20. Koepp AE, Hezari M, Zajicek J, Vogel BS, LaFever RE, Lewis NG, Croteau R (1995) J Biol Chem 270:8686

    CAS  Google Scholar 

  21. Mukaiyama T, Shiina I, Iwadare H, Saitoh M, Nishimura T, Ohkawa N, Sakoh H, Nishimura K, Tani Y-I, Hasegawa M, Yamada K, Saitoh K (1999) Chem Eur J 5:121

    CAS  Google Scholar 

  22. Danishefsky SJ, Masters JJ, Young WB, Link JT, Snyder LB, Magee TV, Jung DK, Isaacs RCA, Bornmann WG, Alaimo CA, Coburn CA, Di Grandi MJ (1996) J Am Chem Soc 118:2843

    CAS  Google Scholar 

  23. Miyaoka H, Honda D, Mitome H, Yamada Y (2002) Tetrahedron Lett 43:7773

    CAS  Google Scholar 

  24. Sandmann G, Albrecht M, Schnurr G, Knörzer O, Böger P (1999) Trends Biotechnol 17:233

    CAS  Google Scholar 

  25. Daum G, Lees ND, Bard M, Dickson R (1998) Yeast 14:1471

    CAS  Google Scholar 

  26. Veen M, Lang C (2004) Appl Microbiol Biot 63:635

    CAS  Google Scholar 

  27. Lees ND, Bard M, Kirsch DR (1999) Crit Rev Biochem Mol Biol 34:33

    CAS  Google Scholar 

  28. Kurihara T, Ueda M, Kamasawa N, Osumi M, Tanaka A (1992) J Biochem (Tokyo) 112:845

    CAS  Google Scholar 

  29. Trocha PJ, Sprinson DB (1976) Arch Biochem Biophys 174:45

    CAS  Google Scholar 

  30. Servouse M, Karst F (1986) Biochem J 240:541

    CAS  Google Scholar 

  31. Dimster-Denk D, Rine J (1996) Mol Cell Biol 16:3981

    CAS  Google Scholar 

  32. Dixon G, Scanlon D, Cooper S, Broad P (1997) J Steroid Biochem Mol Biol 62:165

    CAS  Google Scholar 

  33. Dimster-Denk D, Rine J, Phillips J, Scherer S, Cundiff P, DeBord K, Gilliland D, Hickman S, Jarvis A, Tong L, Ashby M (1999) J Lipid Res 40:850

    CAS  Google Scholar 

  34. Campobasso N, Patel M, Wilding IE, Kallender H, Rosenberg M, Gwynn MN (2004) J Biol Chem 279:44883

    CAS  Google Scholar 

  35. Basson ME, Thorsness M, Rine J (1986) Proc Natl Acad Sci USA 83:5563

    CAS  Google Scholar 

  36. Dorsey JK, Porter JW (1968) J Biol Chem 243:4667

    CAS  Google Scholar 

  37. Anderson MS, Muehlbacher M, Street IP, Proffitt J, Poulter CD (1989) J Biol Chem 264:19169

    CAS  Google Scholar 

  38. Barkley SJ, Cornish RM, Poulter CD (2004) J Bacteriol 186:1811

    CAS  Google Scholar 

  39. Kaneda K, Kuzuyama T, Takagi M, Seto H (2001) Proc Natl Acad Sci 98:932

    CAS  Google Scholar 

  40. Bergès T, Guyonnet D, Karst F (1997) J Bacteriol 179:4664

    Google Scholar 

  41. Eberhardt NL, Rilling HC (1975) J Biol Chem 250:863

    CAS  Google Scholar 

  42. Reed BC, Rilling HC (1975) Biochemistry 14:50

    CAS  Google Scholar 

  43. Barnard GF, Langton B, Popjak G (1978) Biochem Biophys Res Commun 85:1097

    Article  CAS  Google Scholar 

  44. Yeh LS, Rilling HC (1977) Arch Biochem Biophys 183:718

    CAS  Google Scholar 

  45. Barnard GF, Popjak G (1981) Biochim Biophys Acta 661:87

    CAS  Google Scholar 

  46. Modis Y, Wierenga RK (1999) Structure Fold Des 7:1279

    CAS  Google Scholar 

  47. Modis Y, Wierenga RK (2000) J Mol Biol 297:1171

    CAS  Google Scholar 

  48. Kursula P, Ojala J, Lambeir AM, Wierenga RK (2002) Biochemistry 41:15543

    CAS  Google Scholar 

  49. Kanayama N, Himeda Y, Atomi H, Ueda M, Tanaka A (1997) J Biochem (Tokyo) 122:616

    CAS  Google Scholar 

  50. Kurihara T, Ueda M, Tanaka A (1989) J Biochem (Tokyo) 106:474

    CAS  Google Scholar 

  51. Kim SA, Copeland L (1997) Appl Environ Microbiol 63:3432

    CAS  Google Scholar 

  52. Theisen MJ, Misra I, Saadat D, Campobasso N, Miziorko HM, Harrison DH (2004) Proc Natl Acad Sci USA 101:16442

    CAS  Google Scholar 

  53. Middleton B (1972) Biochem J 126:35

    CAS  Google Scholar 

  54. Cabano J, Buesa C, Hegardt FG, Marrero PF (1997) Insect Biochem Mol Biol 27:499

    CAS  Google Scholar 

  55. Middleton B, Tubbs PK (1975) Methods Enzymol 35:173

    CAS  Google Scholar 

  56. Istvan ES, Deisenhofer J (2001) Science 292:1160

    CAS  Google Scholar 

  57. Durr IF, Rudney H (1960) J Biol Chem 235:2572

    CAS  Google Scholar 

  58. Yang D, Shipman LW, Roessner CA, Scott AI, Sacchettini JC (2002) J Biol Chem 277:9462

    CAS  Google Scholar 

  59. Gray JC, Kekwick RG (1972) Biochim Biophys Acta 279:290

    CAS  Google Scholar 

  60. Tchen TT (1958) J Biol Chem 233:1100

    CAS  Google Scholar 

  61. Porter JW (1985) Methods Enzymol 110:71

    CAS  Google Scholar 

  62. Romanowski MJ, Bonanno JB, Burley SK (2002) Proteins 47:568

    CAS  Google Scholar 

  63. Bloch K, Chaykin S, Phillips AH, De Waard A (1959) J Biol Chem 234:2595

    CAS  Google Scholar 

  64. Bonanno JB, Edo C, Eswar N, Pieper U, Romanowski MJ, Ilyin V, Gerchman SE, Kycia H, Studier FW, Sali A, Burley SK (2001) Proc Natl Acad Sci USA 98:12896

    CAS  Google Scholar 

  65. Durbecq V, Sainz G, Oudjama Y, Clantin B, Bompard-Gilles C, Tricot C, Caillet J, Stalon V, Droogmans L, Villeret V (2001) EMBO J 20:1530

    CAS  Google Scholar 

  66. Wouters J, Oudjama Y, Ghosh S, Stalon V, Droogmans L, Oldfield E (2003) J Am Chem Soc 125:3198

    CAS  Google Scholar 

  67. Steinbacher S, Kaiser J, Eisenreich W, Huber R, Bacher A, Rohdich F (2003) J Biol Chem 278:18401

    CAS  Google Scholar 

  68. Reardpon JE, Abeles RH (1985) J Am Chem Soc 107:4078

    Google Scholar 

  69. Agranoff BW, Eggerer H, Henning U, Lynen F (1960) J Biol Chem 235:326

    CAS  Google Scholar 

  70. Street IP, Poulter CD (1990) Biochemistry 29:7531

    CAS  Google Scholar 

  71. Rilling HC (1985) Methods Enzymol 110:145

    CAS  Google Scholar 

  72. Bartlett DL, King CH, Poulter CD (1985) Methods Enzymol 110:171

    Article  CAS  Google Scholar 

  73. Goldstein JL, Brown MS (1990) Nature 343:425

    CAS  Google Scholar 

  74. Hampton R, Dimster-Denk D, Rine J (1996) Trends Biochem Sci 21:140

    CAS  Google Scholar 

  75. Hampton RY (1998) Curr Opin Lipidol 9:93

    CAS  Google Scholar 

  76. Thorsness M, Schafer W, D'Ari L, Rine J (1989) Mol Cell Biol 9:5702

    CAS  Google Scholar 

  77. Dimster-Denk D, Thorsness MK, Rine J (1994) Mol Biol Cell 5:655

    CAS  Google Scholar 

  78. Hampton RY, Rine J (1994) J Cell Biol 125:299

    CAS  Google Scholar 

  79. Nakanishi M, Goldstein JL, Brown MS (1988) J Biol Chem 263:8929

    CAS  Google Scholar 

  80. Shearer AG, Hampton RY (2004) J Biol Chem 279:188

    CAS  Google Scholar 

  81. Hampton RY, Bhakta H (1997) Proc Natl Acad Sci USA 94:12944

    CAS  Google Scholar 

  82. Gardner RG, Hampton RY (1999) J Biol Chem 274:31671

    CAS  Google Scholar 

  83. Gardner RG, Shan H, Matsuda SP, Hampton RY (2001) J Biol Chem 276:8681

    CAS  Google Scholar 

  84. Casey WM, Keesler GA, Parks LW (1992) J Bacteriol 174:7283

    CAS  Google Scholar 

  85. Hornby JM, Jensen EC, Lisec AD, Tasto JJ, Jahnke B, Shoemaker R, Dussault P, Nickerson KW (2001) Appl Environ Microbiol 67:2982

    CAS  Google Scholar 

  86. Grabińska K, Palamarczyk G (2002) FEMS Yeast Res 2:259

    Google Scholar 

  87. Haug JS, Goldner CM, Yazlovitskaya EM, Voziyan PA, Melnykovych G (1994) Biochim Biophys Acta 1223:133

    CAS  Google Scholar 

  88. Melnykovych G, Haug JS, Goldner CM (1992) Biochem Biophys Res Commun 186:543

    CAS  Google Scholar 

  89. Machida K, Tanaka T, Fujita K, Taniguchi M (1998) J Bacteriol 180:4460

    CAS  Google Scholar 

  90. Brown MS, Goldstein JL (1980) J Lipid Res 21:505

    CAS  Google Scholar 

  91. Szkopińska A, Świeżewska E, Karst F (2000) Biochem Biophys Res Commun 267:473

    Google Scholar 

  92. Grabowska D, Karst F, Szkopińska A (1998) FEBS Lett 434:406

    CAS  Google Scholar 

  93. Karst F, Plochocka D, Meyer S, Szkopińska A (2004) Cell Biol Int 28:193

    CAS  Google Scholar 

  94. Gillman EC, Slusher LB, Martin NC, Hopper AK (1991) Mol Cell Biol 11:2382

    CAS  Google Scholar 

  95. Kamińska J, Grabińska K, Kwapisz M, Sikora J, Smagowicz WJ, Palamarczyk G, _Zołądek T, Boguta M (2002) FEMS Yeast Res 2:31

    Google Scholar 

  96. Zhou D, White RH (1991) Biochem J 273:627

    CAS  Google Scholar 

  97. Cane DE, Rossi T, Pachlatko JP (1979) Tetrahedron Lett 20:3639

    Google Scholar 

  98. Cane DE, Rossi T, Tillman AM, Pachlatko JP (1981) J Am Chem Soc 103:1838

    CAS  Google Scholar 

  99. Flesch G, Rohmer M (1988) Eur J Biochem 175:405

    CAS  Google Scholar 

  100. Sprenger GA, Schörken U, Wiegert T, Grolle S, de Graaf AA, Taylor SV, Begley TP, Bringer-Meyer S, Sahm H (1997) Proc Natl Acad Sci USA 94:12857

    CAS  Google Scholar 

  101. Lois L-M, Campos N, Putra SR, Danielsen K, Rohmer M, Boronat A (1998) Proc Natl Acad Sci USA 95:2105

    CAS  Google Scholar 

  102. Lange BM, Wildung MR, McCaskill D, Croteau R (1998) Proc Natl Acad Sci USA 95:2100

    CAS  Google Scholar 

  103. Wilding EI, Brown JR, Bryant AP, Chalker AF, Holmes DJ, Ingraham KA, Iordanescu S, So CY, Rosenberg M, Gwynn MN (2000) J Bacteriol 182:4319

    CAS  Google Scholar 

  104. Hedl M, Sutherlin A, Wilding EI, Mazzulla M, McDevitt D, Lane P, Burgner JW, Lehnbeuter KR, Stauffacher CV, Gwynn MN, Rodwell VW (2002) J Bacteriol 184:2116

    CAS  Google Scholar 

  105. Bochar DA, Stauffacher CV, Rodwell VW (1999) Mol Genet Metab 66:122

    CAS  Google Scholar 

  106. Doolittle WF, Logsdon JM (1998) Curr Biol 8:209

    Google Scholar 

  107. Takagi M, Kuzuyama T, Takahashi S, Seto H (2000) J Bacteriol 182:4153

    CAS  Google Scholar 

  108. Hamano Y, Dairi T, Yamamoto M, Kawasaki T, Kaneda K, Kuzuyama T, Itoh N, Seto H (2001) Biosci Biotechnol Biochem 65:1627

    CAS  Google Scholar 

  109. Hamano Y, Dairi T, Yamamoto M, Kuzuyama T, Itoh N, Seto H (2002) Biosci Biotechnol Biochem 66:808

    CAS  Google Scholar 

  110. Kawasaki T, Kuzuyama T, Furihata K, Itoh N, Seto H, Dairi T (2003) J Antibiot (Tokyo) 56:957

    CAS  Google Scholar 

  111. Begley M, Gahan CG, Kollas AK, Hintz M, Hill C, Jomaa H, Eberl M (2004) FEBS Lett 561:99

    CAS  Google Scholar 

  112. Rodríguez-Concepción M, Boronat A (2002) Plant Physiol 130:1079

    Google Scholar 

  113. Eisenreich W, Bacher A, Arigoni D, Rohdich F (2004) Cell Mol Life Sci 61:1401

    CAS  Google Scholar 

  114. Eubanks LM, Poulter CD (2003) Biochemistry 42:1140

    CAS  Google Scholar 

  115. Takahashi S, Kuzuyama T, Watanabe H, Seto H (1998) Proc Natl Acad Sci USA 95:9879

    CAS  Google Scholar 

  116. Kuzuyama T, Takahashi S, Takagi M, Seto H (2000) J Biol Chem 275:19928

    CAS  Google Scholar 

  117. Hoeffler J-F, Tritsch D, Grosdemange-Billiard C, Rohmer M (2002) Eur J Biochem 269:4446

    CAS  Google Scholar 

  118. Proteau PJ (2004) Bioorg Chem 32:483

    CAS  Google Scholar 

  119. Kuzuyama T (2002) Biosci Biotechnol Biochem 66:1619

    CAS  Google Scholar 

  120. Campos N, Rodríguez-Concepción M, Sauret-Güeto S, Gallego F, Lois L-M, Boronat A (2001) Biochem J 353:59

    CAS  Google Scholar 

  121. Rohdich F, Wungsintaweekul J, Fellermeier M, Sagner S, Herz S, Kis K, Eisenreich W, Bacher A, Zenk MH (1999) Proc Natl Acad Sci USA 96:11758

    CAS  Google Scholar 

  122. Kuzuyama T, Takagi M, Kaneda K, Dairi T, Seto H (2000) Tetrahedron Lett 41:703

    CAS  Google Scholar 

  123. Hunter WN, Bond CS, Gabrielsen M, Kemp LE (2003) Biochem Soc Trans 31:537

    CAS  Google Scholar 

  124. Lüttgen H, Rohdich F, Herz S, Wungsintaweekul J, Hecht S, Schuhr CA, Fellermeier M, Sagner S, Zenk MH, Bacher A, Eisenreich W (2000) Proc Natl Acad Sci USA 97:1062

    Google Scholar 

  125. Kuzuyama T, Takagi M, Kaneda K, Dairi T, Seto H (2000) Tetrahedron Lett 41:2925

    CAS  Google Scholar 

  126. Miallau L, Alphey MS, Kemp LE, Leonard GA, McSweeney SM, Hecht S, Bacher A, Eisenreich W, Rohdich F, Hunter WN (2003) Proc Natl Acad Sci USA 100:9173

    CAS  Google Scholar 

  127. Takagi M, Kuzuyama T, Kaneda K, Dairi T, Seto H (2000) Tetrahedron Lett 41:3395

    CAS  Google Scholar 

  128. Herz S, Wungsintaweekul J, Schuhr CA, Hecht S, Lüttgen H, Sagner S, Fellermeier M, Eisenreich W, Zenk MH, Bacher A, Rohdich F (2000) Proc Natl Acad Sci USA 97:2486

    CAS  Google Scholar 

  129. Freiberg C, Wieland B, Spaltmann F, Ehlert K, Brotz H, Labischinski H (2001) J Mol Microbiol Biotechnol 3:483

    CAS  Google Scholar 

  130. Campbell TL, Brown ED (2002) J Bacteriol 184:5609

    CAS  Google Scholar 

  131. Gabrielsen M, Bond CS, Hallyburton I, Hecht S, Bacher A, Eisenreich W, Rohdich F, Hunter WN (2004) J Biol Chem

    Google Scholar 

  132. Rodríguez-Concepción M, Campos N, Maria LL, Maldonado C, Hoeffler J-F, Grosdemange-Billiard C, Rohmer M, Boronat A (2000) FEBS Lett 473:328

    Google Scholar 

  133. Giner J-L, Jaun B, Arigoni D (1998) J Chem Soc Chem Commun 1857

    Google Scholar 

  134. Charon L, Hoeffler J-F, Pale-Grosdemange C, Lois L-M, Campos N, Boronat A, Rohmer M (2000) Biochem J 346:737

    CAS  Google Scholar 

  135. Hintz M, Reichenberg A, Altincicek B, Bahr U, Gschwind RM, Kollas AK, Beck E, Wiesner J, Eberl M, Jomaa H (2001) FEBS Lett 509:317

    CAS  Google Scholar 

  136. Altincicek B, Kollas AK, Sanderbrand S, Wiesner J, Hintz M, Beck E, Jomaa H (2001) J Bacteriol 183:2411

    CAS  Google Scholar 

  137. Altincicek B, Kollas A, Eberl M, Wiesner J, Sanderbrand S, Hintz M, Beck E, Jomaa H (2001) FEBS Lett 499:37

    CAS  Google Scholar 

  138. Hecht S, Eisenreich W, Adam P, Amslinger S, Kis K, Bacher A, Arigoni D, Rohdich F (2001) Proc Natl Acad Sci USA 98:14837

    CAS  Google Scholar 

  139. Steinbacher S, Kaiser J, Wungsintaweekul J, Hecht S, Eisenreich W, Gerhardt S, Bacher A, Rohdich F (2002) J Mol Biol 316:79

    CAS  Google Scholar 

  140. Campos N, Rodríguez-Concepción M, Seemann M, Rohmer M, Boronat A (2001) FEBS Lett 488:170

    CAS  Google Scholar 

  141. Seemann M, Bui BT, Wolff M, Tritsch D, Campos N, Boronat A, Marquet A, Rohmer M (2002) Angew Chem Int Edit 41:4337

    CAS  Google Scholar 

  142. Altincicek B, Duin EC, Reichenberg A, Hedderich R, Kollas AK, Hintz M, Wagner S, Wiesner J, Beck E, Jomaa H (2002) FEBS Lett 532:437

    CAS  Google Scholar 

  143. Eberl M, Hintz M, Reichenberg A, Kollas AK, Wiesner J, Jomaa H (2003) FEBS Lett 544:4

    CAS  Google Scholar 

  144. Wolff M, Seemann M, Tse Sum BB, Frapart Y, Tritsch D, Garcia EA, Rodríguez-Concepción M, Boronat A, Marquet A, Rohmer M (2003) FEBS Lett 541:115

    CAS  Google Scholar 

  145. Brandt W, Dessoy MA, Fulhorst M, Gao W, Zenk MH, Wessjohann LA (2004) Chem Biochem 5:311

    CAS  Google Scholar 

  146. Hahn FM, Hurlburt AP, Poulter CD (1999) J Bacteriol 181:4499

    CAS  Google Scholar 

  147. Cunningham FX, Lafond TP, Gantt E (2000) J Bacteriol 182:5841

    CAS  Google Scholar 

  148. Kajiwara S, Fraser PD, Kondo K, Misawa N (1997) Biochem J 324:421

    CAS  Google Scholar 

  149. Wang C-W, Oh M-K, Liao JC (1999) Biotechnol Bioeng 62:235

    CAS  Google Scholar 

  150. Hoeffler J-F, Hemmerlin A, Grosdemange-Billiard C, Bach TJ, Rohmer M (2002) Biochem J 366:573

    CAS  Google Scholar 

  151. Kuzuyama T, Takagi M, Takahashi S, Seto H (2000) J Bacteriol 182:891

    CAS  Google Scholar 

  152. Yajima S, Nonaka T, Kuzuyama T, Seto H, Ohsawa K (2002) J Biochem (Tokyo) 131:313

    CAS  Google Scholar 

  153. Reuter K, Sanderbrand S, Jomaa H, Wiesner J, Steinbrecher I, Beck E, Hintz M, Klebe G, Stubbs MT (2002) J Biol Chem 277:5378

    CAS  Google Scholar 

  154. Grolle S, Bringer-Meyer S, Sahm H (2000) FEMS Microbiol Lett 191:131

    CAS  Google Scholar 

  155. Koppisch AT, Fox DT, Blagg BS, Poulter CD (2002) Biochemistry 41:236

    CAS  Google Scholar 

  156. Richard SB, Bowman ME, Kwiatkowski W, Kang I, Chow C, Lillo AM, Cane DE, Noel JP (2001) Nat Struct Biol 8:641

    CAS  Google Scholar 

  157. Kemp LE, Bond CS, Hunter WN (2001) Acta Crystallogr D Biol Crystallogr 57:1189

    CAS  Google Scholar 

  158. Rohdich F, Wungsintaweekul J, Lüttgen H, Fischer M, Eisenreich W, Schuhr CA, Fellermeier M, Schramek N, Zenk MH, Bacher A (2000) Proc Natl Acad Sci USA 97:8251

    CAS  Google Scholar 

  159. Richard SB, Ferrer JL, Bowman ME, Lillo AM, Tetzlaff CN, Cane DE, Noel JP (2002) J Biol Chem 277:8667

    CAS  Google Scholar 

  160. Kishida H, Wada T, Unzai S, Kuzuyama T, Takagi M, Terada T, Shirouzu M, Yokoyama S, Tame JR, Park SY (2003) Acta Crystallogr D Biol Crystallogr 59:23

    Google Scholar 

  161. Rohdich F, Zepeck F, Adam P, Hecht S, Kaiser J, Laupitz R, Grawert T, Amslinger S, Eisenreich W, Bacher A, Arigoni D (2003) Proc Natl Acad Sci USA 100:1586

    CAS  Google Scholar 

  162. Kollas AK, Duin EC, Eberl M, Altincicek B, Hintz M, Reichenberg A, Henschker D, Henne A, Steinbrecher I, Ostrovsky DN, Hedderich R, Beck E, Jomaa H, Wiesner J (2002) FEBS Lett 532:432

    CAS  Google Scholar 

  163. Marshall JH, Wilmoth GJ (1981) J Bacteriol 147:900

    CAS  Google Scholar 

  164. Johnson EA, Schroeder WA (1996) Adv Biochem Eng Biotechnol 53:119

    CAS  Google Scholar 

  165. Misawa N, Nakagawa M, Kobayashi K, Yamano S, Izawa Y, Nakamura K, Harashima K (1990) J Bacteriol 172:6704

    CAS  Google Scholar 

  166. Lee PC, Schmidt-Dannert C (2002) Appl Microbiol Biot 60:1

    CAS  Google Scholar 

  167. Schmidt-Dannert C (2000) Curr Opin Biotechnol 11:255

    CAS  Google Scholar 

  168. Arthington-Skaggs BA, Crowell DN, Yang H, Sturley SL, Bard M (1996) FEBS Lett 392:161

    CAS  Google Scholar 

  169. Yamano S, Ishii T, Nakagawa M, Ikenaga H, Misawa N (1994) Biosci Biotechnol Biochem 58:1112

    Article  CAS  Google Scholar 

  170. Miura Y, Kondo K, Shimada H, Saito T, Nakamura K, Misawa N (1998) Biotechnol Bioeng 58:306

    CAS  Google Scholar 

  171. Miura Y, Kondo K, Saito T, Shimada H, Fraser PD, Misawa N (1998) Appl Environ Microbiol 64:1226

    CAS  Google Scholar 

  172. Shimada H, Kondo K, Fraser PD, Miura Y, Saito T, Misawa N (1998) Appl Environ Microbiol 64:2676

    CAS  Google Scholar 

  173. Huang Q, Roessner CA, Croteau R, Scott AI (2001) Bioorg Med Chem 9:2237

    CAS  Google Scholar 

  174. Reiling KK, Yoshikuni Y, Martin VJJ, Newman J, Bohlmann J, Keasling JD (2004) Biotechnol Bioeng 87:200

    CAS  Google Scholar 

  175. Martin VJJ, Yoshikuni Y, Keasling JD (2001) Biotechnol Bioeng 75:497

    CAS  Google Scholar 

  176. Martin VJJ, Pitera DJ, Withers ST, Newman JD, Keasling JD (2003) Nat Biotechnol 21:796

    CAS  Google Scholar 

  177. Wang C-W, Oh M-K, Liao JC (2000) Biotechnol Prog 16:922

    CAS  Google Scholar 

  178. Matthews PD, Wurtzel ET (2000) Appl Microbiol Biot 53:396

    CAS  Google Scholar 

  179. Harker M, Bramley PM (1999) FEBS Lett 448:115

    CAS  Google Scholar 

  180. Kim S-W, Keasling JD (2001) Biotechnol Bioeng 72:408

    CAS  Google Scholar 

  181. Albrecht M, Misawa N, Sandmann G (1999) Biotechnol Lett 21:791

    CAS  Google Scholar 

  182. Kingston DGI (2001) Chem Commun 1:867

    Article  Google Scholar 

  183. Sandmann G (2001) Trends Plant Sci 6:14

    CAS  Google Scholar 

  184. Ruther A, Misawa N, Böger P, Sandmann G (1997) Appl Microbiol Biot 48:162

    CAS  Google Scholar 

  185. Farmer WR, Liao JC (2001) Biotechnol Prog 17:57

    CAS  Google Scholar 

  186. Wang G-Y, Keasling JD (2002) Metab Eng 4:193

    CAS  Google Scholar 

  187. Jackson BE, Hart-Wells EA, Matsuda SPT (2003) Org Lett 5:1629

    CAS  Google Scholar 

  188. Tapiero H, Townsend DM, Tew KD (2004) Biomed Pharmacother 58:100

    CAS  Google Scholar 

  189. Nishino H (1998) Mutat Res 402:159

    CAS  Google Scholar 

  190. Johnson EJ (2002) Nutr Clin Care 5:56

    Google Scholar 

  191. Cooper DA, Eldridge AL, Peters JC (1999) Nutr Rev 57:201

    Article  CAS  Google Scholar 

  192. Albrecht M, Takaichi S, Misawa N, Schnurr G, Böger P, Sandmann G (1997) J Biotechnol 58:177

    CAS  Google Scholar 

  193. Albrecht M, Takaichi S, Steiger S, Wang Z-Y, Sandmann G (2000) Nat Biotechnol 18:843

    CAS  Google Scholar 

  194. Yokoyama A, Shizuri Y, Misawa N (1998) Tetrahedron Lett 39:3709

    CAS  Google Scholar 

  195. Steiger S, Takaichi S, Sandmann G (2002) J Biotechnol 97:51

    CAS  Google Scholar 

  196. Schmidt-Dannert C, Umeno D, Arnold FH (2000) Nat Biotechnol 18:750

    CAS  Google Scholar 

  197. Carter OA, Peters RJ, Croteau R (2003) Phytochem 64:425

    CAS  Google Scholar 

  198. Misawa N, Yamano S, Ikenaga H (1991) Appl Environ Microbiol 57:1847

    CAS  Google Scholar 

  199. Edwards JS, Palsson BØ (2000) Proc Natl Acad Sci USA 97:5528

    CAS  Google Scholar 

  200. Reed JL, Vo TD, Schilling CH, Palsson BØ (2003) Genome Biol 4:54

    Google Scholar 

  201. Förster J, Famili I, Fu P, Palsson BØ, Nielsen J (2003) Genome Res 13:244

    Google Scholar 

  202. Patil KR, Åkesson M, Nielsen J (2004) Curr Opin Biotechnol 15:64

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jens Nielsen .

Editor information

J. Nielsen

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Maury, J., Asadollahi, M.A., Møller, K., Clark, A., Nielsen, J. Microbial Isoprenoid Production: An Example of Green Chemistry through Metabolic Engineering . In: Nielsen, J. (eds) Biotechnology for the Future. Advances in Biochemical Engineering/Biotechnology, vol 100. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136410

Download citation

Publish with us

Policies and ethics