Skip to main content

Advertisement

Log in

Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis

  • Minireview
  • Published:
JBIC Journal of Biological Inorganic Chemistry Aims and scope Submit manuscript

Abstract

Increasing levels of energy consumption, dwindling resources, and environmental considerations have served as compelling motivations to explore renewable alternatives to petroleum-based fuels, including enzymatic routes for hydrocarbon synthesis. Phylogenetically diverse species have long been recognized to produce hydrocarbons, but many of the enzymes responsible have been identified within the past decade. The enzymatic conversion of Cn chain length fatty aldehydes (or acids) to Cn-1 hydrocarbons, alkanes or alkenes, involves a C–C scission reaction. Surprisingly, the enzymes involved in hydrocarbon synthesis utilize non-heme mononuclear iron, dinuclear iron, and thiolate-ligated heme cofactors that are most often associated with monooxygenation reactions. In this review, we examine the mechanisms of several enzymes involved in hydrocarbon biosynthesis, with specific emphasis on the structural and electronic changes that enable this functional switch.

Graphical abstract

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Hill J, Nelson E, Tilman D, Polasky S, Tiffany D (2006) Proc Natl Acad Sci USA 103:11206–11210

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Brennan L, Owende P (2010) Renew Sustain Energy Rev 14:557–577

    Article  CAS  Google Scholar 

  3. Carroll A, Somerville C (2009) Annu Rev Plant Biol 60:165–182

    Article  CAS  PubMed  Google Scholar 

  4. Van Dyk JS, Pletschke BI (2012) Biotechnol Adv 30:1458–1480

    Article  PubMed  CAS  Google Scholar 

  5. Liao JC, Mi L, Pontrelli S, Luo SS (2016) Nat Rev Microbiol 14:288–304

    Article  CAS  PubMed  Google Scholar 

  6. Liu TG, Khosla C (2010) Annu Rev Genet 44:53–69

    Article  CAS  PubMed  Google Scholar 

  7. Peralta-Yahya PP, Keasling JD (2010) Biotechnol J 5:147–162

    Article  CAS  PubMed  Google Scholar 

  8. Rabinovitch-Deere CA, Oliver JWK, Rodriguez GM, Atsumi S (2013) Chem Rev 113:4611–4632

    Article  CAS  PubMed  Google Scholar 

  9. Lu XF, Vora H, Khosla C (2008) Metab Eng 10:333–339

    Article  CAS  PubMed  Google Scholar 

  10. Xu P, Gu Q, Wang WY, Wong L, Bower AGW, Collins CH, Koffas MAG (2013) Nat Commun 4:1409–1416

    Article  PubMed  CAS  Google Scholar 

  11. Zhou YJJ, Buijs NA, Zhu ZW, Qin JF, Siewers V, Nielsen J (2016) Nat Commun 7:11709–11717

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Qiu Y, Tittiger C, Wicker-Thomas C, Le Goff G, Young S, Wajnberg E, Fricaux T, Taquet N, Blomquist GJ, Feyereisen R (2012) Proc Natl Acad Sci USA 109:14858–14863

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Lea-Smith DJ, Ortiz-Suarez ML, Lenn T, Nurnberg DJ, Baers LL, Davey MP, Parolini L, Huber RG, Cotton CA, Mastroianni G, Bombelli P, Ungerer P, Stevens TJ, Smith AG, Bond PJ, Mullineaux CW, Howe CJ (2016) Plant Physiol 172:1928–1940

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Krebs C, Fujimori DG, Walsh CT, Bollinger JM (2007) Acc Chem Res 40:484–492

    Article  CAS  PubMed  Google Scholar 

  15. Krest CM, Onderko EL, Yosca TH, Calixto JC, Karp RF, Livada J, Rittle J, Green MT (2013) J Biol Chem 288:17074–17081

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Que L (2007) Acc Chem Res 40:493–500

    Article  CAS  PubMed  Google Scholar 

  17. Groves JT, McClusky GA (1976) J Am Chem Soc 98:859–861

    Article  CAS  Google Scholar 

  18. Groves JT, McClusky GA, White RE, Coon MJ (1978) Biochem Biophys Res Commun 81:154–160

    Article  CAS  PubMed  Google Scholar 

  19. Han J, Chan HWS, Calvin M (1969) J Am Chem Soc 91:5156–5159

    Article  CAS  PubMed  Google Scholar 

  20. Winters K, Parker PL, Van Baalen C (1969) Science 163:467–468

    Article  CAS  PubMed  Google Scholar 

  21. Schirmer A, Rude MA, Li X, Popova E, del Cardayre SB (2010) Science 329:559–562

    Article  CAS  PubMed  Google Scholar 

  22. Cheesbrough TM, Kolattukudy PE (1984) Proc Natl Acad Sci USA 81:6613–6617

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Cheesbrough TM, Kolattukudy PE (1988) J Biol Chem 263:2738–2743

    CAS  PubMed  Google Scholar 

  24. Dennis M, Kolattukudy PE (1992) Proc Natl Acad Sci USA 89:5306–5310

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Lawson DM, Artymiuk PJ, Yewdall SJ, Smith JMA, Livingstone JC, Treffry A, Luzzago A, Levi S, Arosio P, Cesareni G, Thomas CD, Shaw WV, Harrison PM (1991) Nature 349:541–544

    Article  CAS  PubMed  Google Scholar 

  26. Nordlund P, Sjoberg BM, Eklund H (1990) Nature 345:593–598

    Article  CAS  PubMed  Google Scholar 

  27. Stubbe J, Riggs-Gelasco P (1998) Trends Biochem Sci 23:438–443

    Article  CAS  PubMed  Google Scholar 

  28. Elango N, Radhakrishnan R, Froland WA, Wallar BJ, Earhart CA, Lipscomb JD, Ohlendorf DH (1997) Protein Sci 6:556–568

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Rosenzweig AC, Frederick CA, Lippard SJ, Nordlund P (1993) Nature 366:537–543

    Article  CAS  PubMed  Google Scholar 

  30. Fox BG, Froland WA, Dege JE, Lipscomb JD (1989) J Biol Chem 264:10023–10033

    CAS  PubMed  Google Scholar 

  31. Bollinger JM, Edmondson DE, Huynh BH, Filley J, Norton JR, Stubbe J (1991) Science 253:292–298

    Article  CAS  PubMed  Google Scholar 

  32. Stirling DI, Colby J, Dalton H (1979) Biochem J 177:361–364

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Tinberg CE, Lippard SJ (2010) Biochemistry 49:7902–7912

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Das D, Eser BE, Han J, Sciore A, Marsh EN (2011) Angew Chem Int Ed Engl 50:7148–7152

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Eser BE, Das D, Han J, Jones PR, Marsh EN (2011) Biochemistry 50:10743–10750

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Aukema KG, Makris TM, Stoian SA, Richman JE, Munck E, Lipscomb JD, Wackett LP (2013) ACS Catal 3:2228–2238

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Eser BE, Das D, Han J, Jones PR, Marsh EN (2012) Biochemistry 51:5703

    Article  CAS  PubMed  Google Scholar 

  38. Li N, Chang WC, Warui DM, Booker SJ, Krebs C, Bollinger JM Jr (2012) Biochemistry 51:7908–7916

    Article  CAS  PubMed  Google Scholar 

  39. Warui DM, Li N, Norgaard H, Krebs C, Bollinger JM Jr, Booker SJ (2011) J Am Chem Soc 133:3316–3319

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Li N, Norgaard H, Warui DM, Booker SJ, Krebs C, Bollinger JM Jr (2011) J Am Chem Soc 133:6158–6161

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Warui DM, Li N, Norgaard H, Krebs C, Bollinger JM, Booker SJ (2011) J Am Chem Soc 133:3316–3319

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Roberts ES, Vaz ADN, Coon MJ (1991) Proc Natl Acad Sci USA 88:8963–8966

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Vaz ADN, Roberts ES, Coon MJ (1991) J Am Chem Soc 113:5886–5887

    Article  CAS  Google Scholar 

  44. Denisov IG, Makris TM, Sligar SG, Schlichting I (2005) Chem Rev 105:2253–2277

    Article  CAS  PubMed  Google Scholar 

  45. Raner GM, Chiang EW, Vaz ADN, Coon MJ (1997) Biochemistry 36:4895–4902

    Article  CAS  PubMed  Google Scholar 

  46. Atkins WM, Sligar SG (1988) Biochemistry 27:1610–1616

    Article  CAS  PubMed  Google Scholar 

  47. Grinkova YV, Denisov IG, McLean MA, Sligar SG (2013) Biochem Biophys Res Commun 430:1223–1227

    Article  CAS  PubMed  Google Scholar 

  48. Nakajin S, Hall PF (1981) J Biol Chem 256:3871–3876

    CAS  PubMed  Google Scholar 

  49. Mak PJ, Gregory MC, Denisov IG, Sligar SG, Kincaid JR (2015) Proc Natl Acad Sci USA 112:15856–15861

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. Banerjee R, Proshlyakov Y, Lipscomb JD, Proshlyakov DA (2015) Nature 518:431–434

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Shu LJ, Nesheim JC, Kauffmann K, Munck E, Lipscomb JD, Que L (1997) Science 275:515–518

    Article  CAS  PubMed  Google Scholar 

  52. Jiang W, Yun D, Saleh L, Barr EW, Xing G, Hoffart LM, Maslak MA, Krebs C, Bollinger JM Jr (2007) Science 316:1188–1191

    Article  CAS  PubMed  Google Scholar 

  53. Jiang W, Yun D, Saleh L, Bollinger JM, Krebs C (2008) Biochemistry 47:13736–13744

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Boal AK, Cotruvo JA, Stubbe J, Rosenzweig AC (2010) Science 329:1526–1530

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Cotruvo JA, Stubbe J (2010) Biochemistry 49:1297–1309

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. Fox BG, Surerus KK, Munck E, Lipscomb JD (1988) J Biol Chem 263:10553–10556

    CAS  PubMed  Google Scholar 

  57. Hendrich MP, Munck E, Fox BG, Lipscomb JD (1990) J Am Chem Soc 112:5861–5865

    Article  CAS  Google Scholar 

  58. Pandelia ME, Li N, Norgaard H, Warui DM, Rajakovich LJ, Chang WC, Booker SJ, Krebs C, Bollinger JM Jr (2013) J Am Chem Soc 135:15801–15812

    Article  CAS  PubMed  Google Scholar 

  59. Rajakovich LJ, Norgaard H, Warui DM, Chang WC, Li N, Booker SJ, Krebs C, Bollinger JM Jr, Pandelia ME (2015) J Am Chem Soc 137:11695–11709

    Article  CAS  PubMed  Google Scholar 

  60. Broadwater JA, Achim C, Munck E, Fox BG (1999) Biochemistry 38:12197–12204

    Article  CAS  PubMed  Google Scholar 

  61. Broadwater JA, Ai J, Loehr TM, Sanders-Loehr J, Fox BG (1998) Biochemistry 37:14664–14671

    Article  CAS  PubMed  Google Scholar 

  62. Bollinger JM, Krebs C, Vicol A, Chen SX, Ley BA, Edmondson DE, Huynh BH (1998) J Am Chem Soc 120:1094–1095

    Article  CAS  Google Scholar 

  63. Moenne-Loccoz P, Baldwin J, Ley BA, Loehr TM, Bollinger JM Jr (1998) Biochemistry 37:14659–14663

    Article  CAS  PubMed  Google Scholar 

  64. Skulan AJ, Brunold TC, Baldwin J, Saleh L, Bollinger JM, Solomon EI (2004) J Am Chem Soc 126:8842–8855

    Article  CAS  PubMed  Google Scholar 

  65. Vu VV, Emerson JP, Martinho M, Kim YS, Munck E, Park MH, Que L Jr (2009) Proc Natl Acad Sci USA 106:14814–14819

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  66. Valentine AM, Stahl SS, Lippard SJ (1999) J Am Chem Soc 121:3876–3887

    Article  CAS  Google Scholar 

  67. Lee SK, Nesheim JC, Lipscomb JD (1993) J Biol Chem 268:21569–21577

    CAS  PubMed  Google Scholar 

  68. Tong WH, Chen S, Lloyd SG, Edmondson DE, Huynh BH, Stubbe J (1996) J Am Chem Soc 118:2107–2108

    Article  CAS  Google Scholar 

  69. Buer BC, Paul B, Das D, Stuckey JA, Marsh EN (2014) ACS Chem Biol 9:2584–2593

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  70. Korboukh VK, Li N, Barr EW, Bollinger JM, Krebs C (2009) J Am Chem Soc 131:13608–13609

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. Li N, Korboukh VK, Krebs C, Bollinger JM (2010) Proc Natl Acad Sci USA 107:15722–15727

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. Komor AJ, Rivard BS, Fan RX, Guo YS, Que L, Lipscomb JD (2016) J Am Chem Soc 138:7411–7421

    Article  CAS  PubMed  Google Scholar 

  73. Makris TM, Vu VV, Meier KK, Komor AJ, Rivard BS, Munck E, Que L Jr, Lipscomb JD (2015) J Am Chem Soc 137:1608–1617

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  74. Choi YS, Zhang HJ, Brunzelle JS, Nair SK, Zhao HM (2008) Proc Natl Acad Sci USA 105:6858–6863

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  75. Knoot CJ, Kovaleva EG, Lipscomb JD (2016) J Biol Inorg Chem 21:589–603

    Article  CAS  PubMed  Google Scholar 

  76. Platter E, Lawson M, Marsh C, Sazinsky MH (2011) Arch Biochem Biophys 508:39–45

    Article  CAS  PubMed  Google Scholar 

  77. Brunold TC, Solomon EI (1999) J Am Chem Soc 121:8277–8287

    Article  CAS  Google Scholar 

  78. Brunold TC, Solomon EI (1999) J Am Chem Soc 121:8288–8295

    Article  CAS  Google Scholar 

  79. Murray LJ, Naik SG, Ortillo DO, Garcia-Serres R, Lee JK, Huynh BH, Lippard SJ (2007) J Am Chem Soc 129:14500–14510

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  80. Paul B, Das D, Ellington B, Marsh EN (2013) J Am Chem Soc 135:5234–5237

    Article  CAS  PubMed  Google Scholar 

  81. Das D, Ellington B, Paul B, Marsh EN (2014) ACS Chem Biol 9:570–577

    Article  CAS  PubMed  Google Scholar 

  82. Waugh MW, Marsh EN (2014) Biochemistry 53:5537–5543

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  83. Shokri A, Que L (2015) J Am Chem Soc 137:7686–7691

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  84. Reed JR, Vanderwel D, Choi SW, Pomonis JG, Reitz RC, Blomquist GJ (1994) Proc Natl Acad Sci USA 91:10000–10004

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  85. Balabanidou V, Kampouraki A, MacLean M, Blomquist GJ, Tittiger C, Juárez MP, Mijailovsky SJ, Chalepakis G, Anthousi A, Lynd A, Antoine S, Hemingway J, Ranson H, Lycett GJ, Vontas J (2016) Proc Natl Acad Sci USA 113:9268–9273

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  86. Chen N, Fan YL, Bai Y, Li XD, Zhang ZF, Liu TX (2016) Insect Biochem Mol Biol 76:84–94

    Article  CAS  PubMed  Google Scholar 

  87. Martinez-Paz P, Morales M, Martinez-Guitarte JL, Morcillo G (2012) Comp Biochem Physiol C-Toxicol Pharmacol 155:333–343

    Article  CAS  PubMed  Google Scholar 

  88. Rettie AE, Sheffels PR, Korzekwa KR, Gonzalez FJ, Philpot RM, Baillie TA (1995) Biochemistry 34:7889–7895

    Article  CAS  PubMed  Google Scholar 

  89. Ghosh D, Griswold J, Erman M, Pangborn W (2009) Nature 457:219–223

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  90. Monk BC, Tomasiak TM, Keniya MV, Huschmann FU, Tyndall JDA, O’Connell JD, Cannon RD, McDonald JG, Rodriguez A, Finer-Moore JS, Stroud RM (2014) Proc Natl Acad Sci USA 111:3865–3870

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  91. Rittle J, Green MT (2010) Science 330:933–937

    Article  CAS  PubMed  Google Scholar 

  92. Reed JR, Quilici DR, Blomquist GJ, Reitz RC (1995) Biochemistry 34:16221–16227

    Article  CAS  PubMed  Google Scholar 

  93. Ortiz de Montellano PR, de Voss JJ (2005) Substrate oxidation by p450 enzymes. Kluwer, New York

    Google Scholar 

  94. Cheesbrough TM, Kolattukudy PE (1988) J Biol Chem 263:2738–2743

    CAS  PubMed  Google Scholar 

  95. Cheesbrough TM, Kolattukudy PE (1984) Proc Natl Acad Sci USA 81:6613–6617

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  96. Dennis MW, Kolattukudy PE (1991) Arch Biochem Biophys 287:268–275

    Article  CAS  PubMed  Google Scholar 

  97. Banerjee A, Sharma R, Chisti Y, Banerjee UC (2002) Crit Rev Biotechnol 22:245–279

    Article  CAS  PubMed  Google Scholar 

  98. Sorigue D, Legeret B, Cuine S, Morales P, Mirabella B, Guedeney G, Li-Beisson Y, Jetter R, Peltier G, Beisson F (2016) Plant Physiol 171:2393–2405

    CAS  PubMed  PubMed Central  Google Scholar 

  99. Aarts MG, Keijzer CJ, Stiekema WJ, Pereira A (1995) Plant Cell 7:2115–2127

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  100. Shanklin J, Achim C, Schmidt H, Fox BG, Munck E (1997) Proc Natl Acad Sci USA 94:2981–2986

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  101. Bai YH, McCoy JG, Levin EJ, Sobrado P, Rajashankar KR, Fox BG, Zhou M (2015) Nature 524:252–256

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  102. Rude MA, Baron TS, Brubaker S, Alibhai M, Del Cardayre SB, Schirmer A (2011) Appl Environ Microbiol 77:1718–1727

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  103. Lee DS, Yamada A, Sugimoto H, Matsunaga I, Ogura H, Ichihara K, Adachi SI, Park SY, Shiro Y (2003) J Biol Chem 278:9761–9767

    Article  CAS  PubMed  Google Scholar 

  104. Piontek K, Strittmatter E, Ullrich R, Grobe G, Pecyna MJ, Kluge M, Scheibner K, Hofrichter M, Plattner DA (2013) J Biol Chem 288:34767–34776

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  105. Belcher J, McLean KJ, Matthews S, Woodward LS, Fisher K, Rigby SEJ, Nelson DR, Potts D, Baynham MT, Parker DA, Leys D, Munro AW (2014) J Biol Chem 289:6535–6550

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  106. Fujishiro T, Shoji O, Nagano S, Sugimoto H, Shiro Y, Watanabe Y (2011) J Biol Chem 286:29941–29950

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  107. Fukuda H, Fujii T, Sukita E, Tazaki M, Nagahama S, Ogawa T (1994) Biochem Biophys Res Commun 201:516–522

    Article  CAS  PubMed  Google Scholar 

  108. Fukuda H, Nakamura K, Sukita E, Ogawa T, Fujii T (1996) J Biochem 119:314–318

    Article  CAS  PubMed  Google Scholar 

  109. Jeong YJ, Kang Y, Han AR, Lee YM, Kotani H, Fukuzumi S, Nam W (2008) Angewandte Chemie Int Edn 47:7321–7324

    Article  CAS  Google Scholar 

  110. Matsunaga I, Yamada A, Lee DS, Obayashi E, Fujiwara N, Kobayashi K, Ogura H, Shiro Y (2002) Biochemistry 41:1886–1892

    Article  CAS  PubMed  Google Scholar 

  111. Grant JL, Hsieh CH, Makris TM (2015) J Am Chem Soc 137:4940–4943

    Article  CAS  PubMed  Google Scholar 

  112. Ren XK, Yorke JA, Taylor E, Zhang T, Zhou WH, Wong LL (2015) Chem Eur J 21:15039–15047

    Article  CAS  PubMed  Google Scholar 

  113. Cryle MJ, De Voss JJ (2004) Chem Commun (Camb). doi:10.1039/b311652b:86-87

    Google Scholar 

  114. Grant JL, Mitchell ME, Makris TM (2016) Proc Natl Acad Sci USA 113:10049–10054

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  115. Kellner DG, Hung SC, Weiss KE, Sligar SG (2002) J Biol Chem 277:9641–9644

    Article  CAS  PubMed  Google Scholar 

  116. Palcic MM, Rutter R, Araiso T, Hager LP, Dunford HB (1980) Biochem Biophys Res Commun 94:1123–1127

    Article  CAS  PubMed  Google Scholar 

  117. Wang X, Peter S, Kinne M, Hofrichter M, Groves JT (2012) J Am Chem Soc 134:12897–12900

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  118. Yosca TH, Rittle J, Krest CM, Onderko EL, Silakov A, Calixto JC, Behan RK, Green MT (2013) Science 342:825–829

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  119. Wang XS, Ullrich R, Hofrichter M, Groves JT (2015) Proc Natl Acad Sci USA 112:3686–3691

    CAS  PubMed  PubMed Central  Google Scholar 

  120. Lambeir AM, Dunford HB, Pickard MA (1987) Eur J Biochem 163:123–127

    Article  CAS  PubMed  Google Scholar 

  121. Atkinson JK, Hollenberg PF, Ingold KU, Johnson CC, Le Tadic M-H, Newcomb M, Putt DA (1994) Biochemistry 33:10630–10637

    Article  CAS  PubMed  Google Scholar 

  122. Atkinson JK, Ingold KU (1993) Biochemistry 32:9209–9214

    Article  CAS  PubMed  Google Scholar 

  123. Auclair K, Hu Z, Little DM, Ortiz de Montellano PR, Groves JT (2002) J Am Chem Soc 124:6020–6027

    Article  CAS  PubMed  Google Scholar 

  124. Cooper HLR, Groves JT (2011) Arch Biochem Biophys 507:111–118

    Article  CAS  PubMed  Google Scholar 

  125. Newcomb M, Lansakara-P DSP, Kim HY, Chandrasena REP, Lippard SJ, Beauvais LG, Murray LJ, Izzo V, Hollenberg PF, Coon MJ (2007) J Org Chem 72:1128–1133

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  126. He X, de Montellano PRO (2004) J Biol Chem 279:39479–39484

    Article  CAS  PubMed  Google Scholar 

  127. Rettie AE, Boberg M, Rettenmeier AW, Baillie TA (1988) J Biol Chem 263:13733–13738

    CAS  PubMed  Google Scholar 

  128. Martinie RJ, Livada J, Chang WC, Green MT, Krebs C, Bollinger JM Jr, Silakov A (2015) J Am Chem Soc 137:6912–6919

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  129. Matthews ML, Krest CM, Barr EW, Vaillancourt FH, Walsh CT, Green MT, Krebs C, Bollinger JM (2009) Biochemistry 48:4331–4343

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  130. Matthews ML, Neumann CS, Miles LA, Grove TL, Booker SJ, Krebs C, Walsh CT, Bollinger JM (2009) Proc Natl Acad Sci USA 106:17723–17728

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  131. Vaillancourt FH, Yin J, Walsh CT (2005) Proc Natl Acad Sci USA 102:10111–10116

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  132. Mitchell AJ, Zhu Q, Maggiolo AO, Ananth NR, Hillwig ML, Liu XY, Boal AK (2016) Nat Chem Biol 12:636

    Article  CAS  PubMed  Google Scholar 

  133. Price JC, Barr EW, Tirupati B, Bollinger JM Jr, Krebs C (2003) Biochemistry 42:7497–7508

    Article  CAS  PubMed  Google Scholar 

  134. Chang WC, Guo YS, Wang C, Butch SE, Rosenzweig AC, Boal AK, Krebs C, Bollinger JM (2014) Science 343:1140–1144

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  135. Liu W, Huang XY, Cheng MJ, Nielsen RJ, Goddard WA, Groves JT (2012) Science 337:1322–1325

    Article  CAS  PubMed  Google Scholar 

  136. Bigi MA, Reed SA, White MC (2011) Nature Chemistry 3:216–222

    Article  CAS  PubMed  Google Scholar 

  137. Dennig A, Kuhn M, Tassoti S, Thiessenhusen A, Gilch S, Bulter T, Haas T, Hall M, Faber K (2015) Angew Chem 54:8819–8822

    Article  CAS  Google Scholar 

  138. Zachos I, Gassmeyer SK, Bauer D, Sieber V, Hollmann F, Kourist R (2015) Chem Commun 51:1918–1921

    Article  CAS  Google Scholar 

  139. Amaya JA, Rutland CD, Makris TM (2016) J Inorg Biochem 158:11–16

    Article  CAS  PubMed  Google Scholar 

  140. Hsieh CH, Makris TM (2016) Biochem Biophys Res Commun 476:462–466

    Article  CAS  PubMed  Google Scholar 

  141. Krest CM, Silakov A, Rittle J, Yosca TH, Onderko EL, Calixto JC, Green MT (2015) Nat Chem 7:696–702

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  142. Faponle AS, Quesne MG, de Visser SP (2016) Chem Eur J 22:5478–5483

    Article  CAS  PubMed  Google Scholar 

  143. Rui Z, Li X, Zhu XJ, Liu J, Domigan B, Barr I, Cate JHD, Zhang WJ (2014) Proc Natl Acad Sci USA 111:18237–18242

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  144. Zechman JM, Labows JN Jr (1985) Can J Microbiol 31:232–237

    Article  CAS  PubMed  Google Scholar 

  145. Koehntop KD, Emerson JP, Que L Jr (2005) J Biol Inorg Chem 10:87–93

    Article  CAS  PubMed  Google Scholar 

  146. Ryle MJ, Liu A, Muthukumaran RB, Ho RY, Koehntop KD, McCracken J, Que L Jr, Hausinger RP (2003) Biochemistry 42:1854–1862

    Article  CAS  PubMed  Google Scholar 

  147. Kovaleva EG, Lipscomb JD (2008) Nat Chem Biol 4:186–193

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  148. Xing G, Diao YH, Hoffart LM, Barr EW, Prabhu KS, Arner RJ, Reddy CC, Krebs C, Bollinger JM (2006) Proc Natl Acad Sci USA 103:6130–6135

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  149. Tamanaha E, Zhang B, Guo Y, Chang WC, Barr EW, Xing G, St Clair J, Ye S, Neese F, Bollinger JM Jr, Krebs C (2016) J Am Chem Soc 138:8862–8874

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  150. Pojer F, Kahlich R, Kammerer B, Li SM, Heide L (2003) J Biol Chem 278:30661–30668

    Article  CAS  PubMed  Google Scholar 

  151. Rui Z, Harris NC, Zhu XJ, Huang W, Zhang WJ (2015) Acs Catalysis 5:7091–7094

    Article  CAS  Google Scholar 

  152. Shanklin J, Whittle E, Fox BG (1994) Biochemistry 33:12787–12794

    Article  CAS  PubMed  Google Scholar 

  153. Behrouzian B, Buist PH (2003) Prostaglandins Leukot Essent Fatty Acids 68:107–112

    Article  CAS  PubMed  Google Scholar 

  154. Shanklin J, Guy JE, Mishra G, Lindqvist Y (2009) J Biol Chem 284:18559–18563

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  155. Buist PH, Behrouzian B (1996) J Am Chem Soc 118:6295–6296

    Article  CAS  Google Scholar 

  156. Cooper HLR, Mishra G, Huang XY, Pender-Cudlip M, Austin RN, Shanklin J, Groves JT (2012) J Am Chem Soc 134:20365–20375

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  157. Jin Y, Lipscomb JD (2001) J Biol Inorg Chem 6:717–725

    Article  CAS  PubMed  Google Scholar 

  158. Broadwater JA, Whittle E, Shanklin J (2002) J Biol Chem 277:15613–15620

    Article  CAS  PubMed  Google Scholar 

  159. Broun P, Shanklin J, Whittle E, Somerville C (1998) Science 282:1315–1317

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

Financial support was provided by an ASPIRE grant from the USC Vice President of Research and a National Science Foundation CAREER Grant 1555066 (to T.M.M.).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Thomas M. Makris.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wise, C.E., Grant, J.L., Amaya, J.A. et al. Divergent mechanisms of iron-containing enzymes for hydrocarbon biosynthesis. J Biol Inorg Chem 22, 221–235 (2017). https://doi.org/10.1007/s00775-016-1425-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00775-016-1425-0

Keywords

Navigation