Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli

Applied Microbiology and Biotechnology

Volumn 81, Issue 5, 2009, Pages 915-925

  Harada, Hisashi ^a   Yu, Fengnian ^b   Okamoto, Sho ^b   Kuzuyama, Tomohisa ^c   Utsumi, Ryutaro ^b   Misawa, Norihiko ^a  

^a KIRIN HOLDINGS CO LTD   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

Humulene; Astaxanthin; Carotenoids; Lycopene; Sesquiterpene

Indexed keywords

ASTAXANTHIN; CAROTENOIDS; DRY CELL WEIGHTS; E. COLI; EFFICIENT SYNTHESES; ISOPENTENYL DIPHOSPHATE ISOMERASE; ISOPRENOIDS; LYCOPENE; METABOLIC PATHWAYS; MEVALONATE PATHWAYS; PHYTOENE; SESQUITERPENE; SYNTHASE; TOTAL AMOUNTS;

CELL CULTURE; ENZYMES; GENES;

ESCHERICHIA COLI;

ACETATE; BACTERIUM; ENZYME ACTIVITY; GENE EXPRESSION; GENETIC ENGINEERING; ISOPRENOID; METABOLISM;

ACETOACETATES; ANIMALS; ESCHERICHIA COLI; GENETIC ENGINEERING; GINGER; METABOLIC NETWORKS AND PATHWAYS; RATS; RECOMBINATION, GENETIC; SACCHAROMYCES CEREVISIAE; SESQUITERPENES; STREPTOMYCES; TERPENES;

ESCHERICHIA COLI; RATTUS; STREPTOMYCES; ZINGIBER ZERUMBET;

EID: 58149151350     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-008-1724-7     Document Type: Article

References (44)

1. M Albrecht N Misawa G Sandmann 1999 Metabolic engineering of the terpenoid biosynthetic pathway of Escherichia coli for production of the carotenoids β-carotene and zeaxanthin Biotechnol Lett 21 791 795
2. H Alper YS Jin JF Moxley G Stephanopoulos 2005 Identifying gene targets for the metabolic engineering of lycopene biosynthesis in Escherichia coli Metab Eng 7 155 164
3. H Alper K Miyaoku G Stephanopoulos 2005 Construction of lycopene-overproducing E. coli strains by combining systematic and combinatorial gene knockout targets Nat Biotechnol 23 612 616
4. JD Bergstrom J Edmond 1985 A radiochemical assay for acetoacetyl-CoA synthetase Anal Biochem 149 358 364
5. Britton G, Liaaen-Jensen S, Pfander H (2001) Carotenoids handbook. Birkhauser, Basel, Boston, Berlin
6. GQ Cai BT Driscoll TC Charles 2000 Requirement for the enzymes acetoacetyl coenzyme A synthetase and poly-3-hydroxybutyrate (PHB) synthase for growth of Sinorhizobium meliloti on PHB cycle intermediates J Bacteriol 182 2113 2118
7. MCY Chang JD Keasling 2006 Production of isoprenoid pharmaceuticals by engineered microbes Nat Chem Biol 2 674 681
8. SK Choi Y Nishida S Matsuda K Adachi H Kasai X Peng S Komemushi W Miki N Misawa 2005 Characterization of β-carotene ketolases, CrtW, from marine bacteria by complementation analysis in Escherichia coli Mar Biotechnol (NY) 7 515 522
9. Connolly JD, Hill RA (1991) Dictionary of terpenoids. Chapman & Hall, London
10. GM Cragg 1998 Paclitaxel (Taxol): a success story with valuable lessons for natural product drug discovery and development Med Res Rev 18 315 331
11. M Enserink 2005 Infectious diseases: source of new hope against malaria is in short supply Science 307 33
12. WR Farmer JC Liao 2000 Improving lycopene production in Escherichia coli by engineering metabolic control Nat Biotechnol 18 533 537
13. PD Fraser Y Miura N Misawa 1997 In vitro characterization of astaxanthin biosynthetic enzymes J Biol Chem 272 6128 6135
14. E Giovannucci A Ascherio EB Rimm MJ Stampfer GA Colditz WC Willett 1995 Intake of carotenoids and retinol in relation to risk of prostate cancer J Nat Can Inst 87 1767 1776
15. M Ito T Fukui M Kamokari T Saito K Tomita 1984 Purification and characterization of acetoacetyl-CoA synthetase from rat liver Biochim Biophys Acta 794 183 193
16. T Iwamoto K Hosoda R Hirano H Kurata A Matsumoto W Miki M Kamiyama H Itakura S Yamamoto K Kondo 2000 Inhibition of low-density lipoprotein oxidation by astaxanthin J Atheroscler Thromb 7 216 222
17. YS Jin G Stephanopoulos 2007 Multi-dimensional gene target search for improving lycopene biosynthesis in Escherichia coli Metab Eng 9 337 347
18. S Kajiwara PD Fraser K Kondo N Misawa 1997 Expression of an exogenous isopentenyl diphosphate isomerase gene enhances isoprenoid biosynthesis in Escherichia coli Biochem J 324 421 426
19. K Kakinuma Y Dekishima Y Matsushima T Eguchi N Misawa M Takagi T Kuzuyama H Seto 2001 New approach to multiply deuterated isoprenoids using triply engineered Escherichia coli and its potential as a tool for mechanistic enzymology J Am Chem Soc 123 1238 1239
20. K Kaneda T Kuzuyama M Takagi Y Hayakawa H Seto 2001 An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp. strain CL190 Proc Nat Acad Sci U S A 98 932 937
21. DM Martin J Gershenzon J Bohlmann 2003 Induction of volatile terpene biosynthesis and diurnal emission by methyl jasmonate in foliage of Norway spruce Plant Physiol 132 1586 1599
22. VJ Martin DJ Pitera ST Withers JD Newman JD Keasling 2003 Engineering a mevalonate pathway in Escherichia coli for production of terpenoids Nat Biotechnol 21 796 802
23. N Misawa M Nakagawa K Kobayashi S Yamano Y Izawa K Nakamura K Harashima 1990 Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli J Bacteriol 172 6704 6712
24. N Misawa Y Satomi K Kondo A Yokoyama S Kajiwara T Saito T Ohtani W Miki 1995 Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level J Bacteriol 177 6575 6584
25. M Nakamoto N Takahashi A Iwahori H Sato T Fukui 1999 Effects of development on acetoacetyl-CoA synthetase biosynthesis in rat liver Biol Pharm Bull 22 981 983
26. JD Newman J Marshal M Chang F Nowroozi E Paradise D Pitera KL Newman JD Keasling 2006 High-level production of amorpha-4,11-diene in a two-phase partitioning bioreactor of metabolically engineered Escherichia coli Biotechnol Bioeng 95 684 691
27. Y Nishida K Adachi H Kasai Y Shizuri K Shindo A Sawabe S Komemushi W Miki N Misawa 2005 Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2,2′-β-hydroxylase, from Brevundimonas sp. strain SD212 and combinatorial biosynthesis of new or rare xanthophylls Appl Environ Microbiol 71 4286 4296
28. M Rohmer M Knani P Simonin B Sutter H Sahm 1993 Isoprenoid biosynthesis in bacteria: a novel pathway for early steps leading to isopentenyl diphosphate Biochem J 295 517 524
29. Sambrook J, Russell DW (2001) Molecular cloning, 3rd edn. Laboratory, Cold Spring Harbor, NY
30. H Sato N Takahashi M Nakamoto M Ohgami M Yamazaki T Fukui 2002 Effects of streptozotocin-induced diabetes on acetoacetyl-CoA synthetase activity in rats Biochem Pharmacol 63 1851 1855
31. H Shimada K Kondo PD Fraser Y Miura T Saito N Misawa 1998 Increased carotenoid production by the food yeast Candida utilis through metabolic engineering of the isoprenoid pathway Appl Environ Microbiol 64 2676 2680
32. SJ Sramek FE Frerman 1975 Purification and properties of Escherichia coli coenzyme A-transferase Arch Biochem Biophys 171 14 26
33. SJ Sramek FE Frerman 1975 Escherichia coli coenzyme A-transferase: kinetics, catalytic pathway and structure Arch Biochem Biophys 171 27 35
34. MJ Stark 1987 Multicopy expression vectors carrying the lac repressor gene for regulated high-level expression of genes in Escherichia coli Gene 15 255 267
35. M Takagi T Kuzuyama S Takahashi H Seto 2000 A gene cluster for the mevalonate pathway from Streptomyces sp. strain CL190 J Bacteriol 182 4153 4157
36. XS Tang J Shyr L Tao N Sedkova Q Cheng 2007 Improvement of a CrtO-type of β-carotene ketolase for canthaxanthin production in Methylomonas sp Metab Eng 9 348 354
37. RV Vadali Y Fu GN Bennett KY San 2005 Enhanced lycopene productivity by manipulation of carbon flow to isopentenyl diphosphate in Escherichia coli Biotechnol Prog 21 1558 1561
38. RW Ye H Yao K Stead T Wang L Tao Q Cheng PL Sharpe W Suh E Nagel D Arcilla D Dragotta ES Miller 2007 Construction of the astaxanthin biosynthetic pathway in a methanotrophic bacterium Methylomonas sp. strain 16a J Ind Microbiol Biotechnol 34 289 299
39. A Yokoyama Y Shizuri N Misawa 1998 Production of new carotenoids, astaxanthin glucosides, by Escherichia coli transformants carrying carotenoid biosynthetic genes Tetrahedron Lett 39 3709 3712
40. SH Yoon YM Lee JE Kim SH Lee JH Lee JY Kim KH Jung YC Shin JD Keasling SW Kim 2006 Enhanced lycopene production in Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate Biotechnol Bioeng 94 1025 1032
41. SH Yoon HM Park JE Kim SH Lee MS Choi JY Kim DK Oh JD Keasling SW Kim 2007 Increased β-carotene production in recombinant Escherichia coli harboring an engineered isoprenoid precursor pathway with mevalonate addition Biotechnol Prog 23 599 605
42. F Yu S Okamoto K Nakasone K Adachi S Matsuda H Harada N Misawa R Utsumi 2008 Molecular cloning and functional characterization of α-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith) Planta 227 1291 1299
43. F Yu H Harada K Yamasaki S Okamoto S Hirase Y Tanaka N Misawa R Utsumi 2008 Isolation and functional characterization of a β-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith FEBS Lett 582 565 572
44. LZ Yuan PE Rouviere W Suh 2006 Chromosomal promoter replacement of the isoprenoid pathway for enhancing carotenoid production in E coli. Metab Eng 8 79 90