Terpenoid biosynthesis in prokaryotes

Advances in Biochemical Engineering/Biotechnology

Volumn 148, Issue , 2015, Pages 3-18

  Boronat, Albert ^a,b   Rodríguez Concepción, Manuel ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Bacteriochlorophylls; Bactoprenol; Carotenoids; Ether type lipids; Heme; Hopanoids; Isopentenyl tRNA; Menaquinone; MEP pathway; MVA pathway; Rhodopsins; Terpenoid; Ubiquinone

Indexed keywords

BACTERIA (MICROORGANISMS); EUKARYOTA; PROKARYOTA;

BACTERIOCHLOROPHYLL; BACTOPRENOL; CAROTENOID; CHLOROPHYLL; FARNOQUINONE; RHODOPSIN; TERPENE; UBIQUINONE;

ARCHAEON; BACTERIUM; CELL MEMBRANE; CELL WALL; CHEMISTRY; DRUG DESIGN; FUNGUS; METABOLISM; MITOCHONDRION; PLASTID;

ARCHAEA; BACTERIA; BACTERIOCHLOROPHYLLS; CAROTENOIDS; CELL MEMBRANE; CELL WALL; CHLOROPHYLL; DRUG DESIGN; FUNGI; MITOCHONDRIA; PLASTIDS; RHODOPSIN; TERPENES; UBIQUINONE; VITAMIN K 2;

EID: 84930198440     PISSN: 07246145     EISSN: None     Source Type: Book Series    
DOI: 10.1007/10_2014_285     Document Type: Article

References (66)

1. Barrios-Gonzalez J, Miranda RU (2010) Biotechnological production and applications of statins. Appl Microbiol Biotechnol 85:869-883
2. Bochar DA, Stauffacher CV, Rodwell VW (1999) Sequence comparisons reveal two classes of 3-hydroxy-3-methylglutaryl coenzyme A reductase. Mol Genet Metab 66:122-127
3. Boucher Y, Doolittle WF (2000) The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways. Mol Microbiol 37:703-716
4. Boucher Y, Kamekura M, Doolittle WF (2004) Origins and evolution of isoprenoid lipid biosynthesis in archaea. Mol Microbiol 52:515-527
5. Boucher Y, Huber H, L’Haridon S, Stetter KO, Doolittle WF (2001) Bacterial origin for the isoprenoid biosynthesis enzyme hmg-coa reductase of the archaeal orders thermoplasmatales and archaeoglobales. Mol Biol Evol 18:1378-1388
6. Bouhss A, Trunkfield AE, Bugg TD, Mengin-Lecreulx D (2008) The biosynthesis of peptidoglycan lipid-linked intermediates. FEMS Microbiol Rev 32:208-233
7. Brown AC, Parish T (2008) Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake. BMC Microbiol 8:78
8. Cane DE, Ikeda H (2012) Exploration and mining of the bacterial terpenome. Acc Chem Res 45:463-472
9. Carretero-Paulet L, Lipska A, Perez-Gil J, Sangari FJ, Albert VA, Rodriguez-Concepcion M (2013) Evolutionary diversification and characterization of the eubacterial gene family encoding DXR type II, an alternative isoprenoid biosynthetic enzyme. BMC Evol Biol 13:180
10. Chen M, Poulter CD (2010) Characterization of thermophilic archaeal isopentenyl phosphate kinases. Biochemistry 49:207-217
11. Chew AG, Bryant DA (2007) Chlorophyll biosynthesis in bacteria: the origins of structural and functional diversity. Annu Rev Microbiol 61:113-129
12. Dairi T (2005) Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes. J Antibiot 58:227-243
13. Dairi T (2013) Biosynthetic genes and enzymes of isoprenoids produced by Actinomycetes. In: Bach T, Rohmer M (eds) Isoprenoid synthesis in plants and microorganisms. Springer, New York, pp 29-49
14. Dellas N, Thomas ST, Manning G, Noel JP (2013) Discovery of a metabolic alternative to the classical mevalonate pathway. Elife 2:e00672
15. Durbecq V, Sainz G, Oudjama Y, Clantin B, Bompard-Gilles C, Tricot C, Caillet J, Stalon V, Droogmans L, Villeret V (2001) Crystal structure of isopentenyl diphosphate: Dimethylallyl diphosphate isomerase. Embo J 20:1530-1537
16. Eberl M, Jomaa H (2003) A genetic basis for human gammadelta T-cell reactivity towards microbial pathogens. Trends Immunol 24:407-409
17. Erb TJ, Evans BS, Cho K, Warlick BP, Sriram J, Wood BM, Imker HJ, Sweedler JV, Tabita FR, Gerlt JA (2012) A RubisCO-like protein links SAM metabolism with isoprenoid biosynthesis. Nat Chem Biol 8:926-932
18. Ershov YV, Gantt RR, Cunningham FX Jr, Gantt E (2002) Isoprenoid biosynthesis in Synechocystis sp. strain PCC6803 is stimulated by compounds of the pentose phosphate cycle but not by pyruvate or deoxyxylulose-5-phosphate. J Bacteriol 184:5045-5051
19. Fuhrman JA, Schwalbach MS, Stingl U (2008) Proteorhodopsins: an array of physiological roles? Nature reviews. Microbiology 6:488-494
20. Fujisaki S, Ohnuma S, Horiuchi T, Takahashi I, Tsukui S, Nishimura Y, Nishino T, Kitabatake M, Inokuchi H (1996) Cloning of a gene from Escherichia coli that confers resistance to fosmidomycin as a consequence of amplification. Gene 175:83-87
21. Grochowski LL, Xu H, White RH (2006) Methanocaldococcus jannaschii uses a modified mevalonate pathway for biosynthesis of isopentenyl diphosphate. J Bacteriol 188:3192-3198
22. Grote M, O’Malley MA (2011) Enlightening the life sciences: the history of halobacterial and microbial rhodopsin research. FEMS Microbiol Rev 35:1082-1099
23. Hederstedt L (2012) Heme A biosynthesis. Biochimica et biophysica acta 1817:920-927
24. Kaneda K, Kuzuyama T, Takagi M, Hayakawa Y, Seto H (2001) An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp. strain CL190. Proc Natl Acad Sci USA 98:932-937
25. Kaneko T, Sato S, Kotani H, Tanaka A, Asamizu E, Nakamura Y, Miyajima N, Hirosawa M, Sugiura M, Sasamoto S, Kimura T, Hosouchi T, Matsuno A, Muraki A, Nakazaki N, Naruo K, Okumura S, Shimpo S, Takeuchi C, Wada T, Watanabe A, Yamada M, Yasuda M, Tabata S (1996) Sequence analysis of the genome of the unicellular cyanobacterium Synechocystis sp. strain PCC6803. II. Sequence determination of the entire genome and assignment of potential protein-coding regions. DNA Res 3:109-136
26. Kannenberg EL, Poralla K (1999) Hopanoid biosynthesis and function in bacteria. Naturwissenschaften 86:168-176
27. Kawamukai M (2002) Biosynthesis, bioproduction and novel roles of ubiquinone. J Biosci Bioeng 94:511-517
28. Koga Y, Morii H (2007) Biosynthesis of ether-type polar lipids in archaea and evolutionary considerations. Microbiol Mol Biol Rev MMBR 71:97-120
29. Kuzuyama T, Seto H (2003) Diversity of the biosynthesis of the isoprene units. Nat Prod Rep 20:171-183
30. Kuzuyama T, Shimizu T, Takahashi S, Seto H (1998) Fosmidomycin, a specific inhibitor of 1-Deoxy-d-Xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis. Tetrahedron Lett 39:7913-7916
31. Laupitz R, Hecht S, Amslinger S, Zepeck F, Kaiser J, Richter G, Schramek N, Steinbacher S, Huber R, Arigoni D, Bacher A, Eisenreich W, Rohdich F (2004) Biochemical characterization of Bacillus subtilis type II isopentenyl diphosphate isomerase, and phylogenetic distribution of isoprenoid biosynthesis pathways. Eur J Biochem 271:2658-2669
32. Leonardi R, Roach PL (2004) Thiamine biosynthesis in Escherichia coli: in vitro reconstitution of the thiazole synthase activity. J Biol Chem 279:17054-17062
33. Lombard J, Moreira D (2011) Origins and early evolution of the mevalonate pathway of isoprenoid biosynthesis in the three domains of life. Mol Biol Evol 28:87-99
34. Lovering AL, Safadi SS, Strynadka NC (2012) Structural perspective of peptidoglycan biosynthesis and assembly. Annu Rev Biochem 81:451-478
35. Mabanglo MF, Schubert HL, Chen M, Hill CP, Poulter CD (2010) X-ray structures of isopentenyl phosphate kinase. ACS Chem Biol 5:517-527
36. Maeda I, Inaba A, Koike H, Yoneyama K, Ueda S, Yoshida K (2013) Acyclic carotenoid and cyclic apocarotenoid cleavage by an orthologue of lignostilbene-alpha, beta-dioxygenase in Rhodopseudomonas palustris. J Biochem 154:449-454
37. Maresca JA, Graham JE, Bryant DA (2008) The biochemical basis for structural diversity in the carotenoids of chlorophototrophic bacteria. Photosynth Res 97:121-140
38. Matsumi R, Atomi H, Driessen AJ, van der Oost J (2011) Isoprenoid biosynthesis in Archaea-biochemical and evolutionary implications. Res Microbiol 162:39-52
39. Meganathan R (2001) Ubiquinone biosynthesis in microorganisms. FEMS Microbiol Lett 203:131-139
40. Mogi T, Saiki K, Anraku Y (1994) Biosynthesis and functional role of haem O and haem A. Mol Microbiol 14:391-398
41. Mukherjee T, Hanes J, Tews I, Ealick SE, Begley TP (2011) Pyridoxal phosphate: biosynthesis and catabolism. Biochim Biophys Acta 1814:1585-1596
42. Perez-Gil J, Calisto BM, Behrendt C, Kurz T, Fita I, Rodriguez-Concepcion M (2012) Crystal structure of Brucella abortus deoxyxylulose-5-phosphate reductoisomerase-like (DRL) enzyme involved in isoprenoid biosynthesis. J Biol Chem 287:15803-15809
43. Perez-Gil J, Uros EM, Sauret-Gueto S, Lois LM, Kirby J, Nishimoto M, Baidoo EE, Keasling JD, Boronat A, Rodriguez-Concepcion M (2012) Mutations in Escherichia coli aceE and ribB genes allow survival of strains defective in the first step of the isoprenoid biosynthesis pathway. PloS one 7:e43775
44. Persson BC, Esberg B, Olafsson O, Bjork GR (1994) Synthesis and function of isopentenyl adenosine derivatives in tRNA. Biochimie 76:1152-1160
45. Phillips MA, Leon P, Boronat A, Rodriguez-Concepcion M (2008) The plastidial MEP pathway: unified nomenclature and resources. Trends Plant Sci 13:619-623
46. Poliquin K, Ershov YV, Cunningham FX Jr, Woreta TT, Gantt RR, Gantt E (2004) Inactivation of sll1556 in Synechocystis strain PCC 6803 impairs isoprenoid biosynthesis from pentose phosphate cycle substrates in vitro. J Bacteriol 186:4685-4693
47. Rodriguez-Concepcion M, Boronat A (2013) Isoprenoid biosynthesis in prokaryotic organisms. In: Bach T, Rohmer M (eds) Isoprenoid synthesis in plants and microorganisms. Springer, New York, pp 1-16
48. Rodríguez-Concepción M, Boronat A (2002) Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics. Plant Physiol 130:1079-1089
49. Rohmer M (2008) From molecular fossils of bacterial hopanoids to the formation of isoprene units: discovery and elucidation of the methylerythritol phosphate pathway. Lipids 43:1095-1107
50. Rothman SC, Johnston JB, Lee S, Walker JR, Poulter CD (2008) Type II isopentenyl diphosphate isomerase: irreversible inactivation by covalent modification of flavin. J Am Chem Soc 130:4906-4913
51. Sakamoto Y, Furukawa S, Ogihara H, Yamasaki M (2003) Fosmidomycin resistance in adenylate cyclase deficient (cya) mutants of Escherichia coli. Biosci Biotechnol Biochem 67:2030-2033
52. Sangari FJ, Perez-Gil J, Carretero-Paulet L, Garcia-Lobo JM, Rodriguez-Concepcion M (2010) A new family of enzymes catalyzing the first committed step of the methylerythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in bacteria. Proc Natl Acad Sci USA 107:14081-14086
53. Sauret-Güeto S, Uros EM, Ibanez E, Boronat A, Rodriguez-Concepcion M (2006) A mutant pyruvate dehydrogenase E1 subunit allows survival of Escherichia coli strains defective in 1-deoxy-D-xylulose 5-phosphate synthase. FEBS Lett 580:736-740
54. Sharma NK, Pan JJ, Poulter CD (2010) Type II isopentenyl diphosphate isomerase: probing the mechanism with alkyne/allene diphosphate substrate analogues. Biochemistry 49:6228-6233
55. Shindo K, Misawa N (2014) New and rare carotenoids isolated from marine bacteria and their antioxidant activities. Mar Drugs 12:1690-1698
56. Siedenburg G, Jendrossek D (2011) Squalene-hopene cyclases. Appl Environ Microbiol 77:3905-3915
57. Smit A, Mushegian A (2000) Biosynthesis of isoprenoids via mevalonate in Archaea: The lost pathway. Genome Res 10:1468-1484
58. Sui X, Kiser PD, Lintig J, Palczewski K (2013) Structural basis of carotenoid cleavage: From bacteria to mammals. Arch Biochem Biophys 539:203-213
59. Unno H, Yamashita S, Ikeda Y, Sekiguchi SY, Yoshida N, Yoshimura T, Kusunoki M, Nakayama T, Nishino T, Hemmi H (2009) New role offlavin as a general acid-base catalyst with no redox function in type 2 isopentenyl-diphosphate isomerase. J Biol Chem 284:9160-9167
60. Van Horn WD, Sanders CR (2012) Prokaryotic diacylglycerol kinase and undecaprenol kinase. Annu Rev Biophys 41:81-101
61. Vannice JC, Skaff DA, Keightley A, Addo JK, Wyckoff GJ, Miziorko HM (2014) Identification in Haloferax volcanii of phosphomevalonate decarboxylase and isopentenyl phosphate kinase as catalysts of the terminal enzyme reactions in an archaeal alternate mevalonate pathway. J Bacteriol 196:1055-1063
62. Vollmer W, Blanot D, de Pedro MA (2008) Peptidoglycan structure and architecture. FEMS Microbiol Rev 32:149-167
63. Warlick BP, Evans BS, Erb TJ, Ramagopal UA, Sriram J, Imker HJ, Sauder JM, Bonanno JB, Burley SK, Tabita FR, Almo SC, Sweedler JS, Gerlt JA (2012) 1-methylthio-D-xylulose 5-phosphate methylsulfurylase: a novel route to 1-deoxy-D-xylulose 5-phosphate in Rhodospirillum rubrum. Biochemistry 51:8324-8326
64. Wouters J, Oudjama Y, Ghosh S, Stalon V, Droogmans L, Oldfield E (2003) Structure and mechanism of action of isopentenylpyrophosphate-dimethylallylpyrophosphate isomerase. J Am Chem Soc 125:3198-3199
65. Xiao Y, Savchenko T, Baidoo EE, Chehab WE, Hayden DM, Tolstikov V, Corwin JA, Kliebenstein DJ, Keasling JD, Dehesh K (2012) Retrograde signaling by the plastidial metabolite MEcPP regulates expression of nuclear stress-response genes. Cell 149:1525-1535
66. Yamada Y, Cane DE, Ikeda H (2012) Diversity and analysis of bacterial terpene synthases. Methods Enzymol 515:123-162