Biosynthesis and engineering of isoprenoid small molecules

Applied Microbiology and Biotechnology

Volumn 73, Issue 5, 2007, Pages 980-990

  Withers, Sydnor T ^a,d   Keasling, Jay D ^a,b,c,d  

^a University of California   (United States)

^b University of California at Berkeley   (United States)

^c Berkeley   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Artemisinin; Isoprenoids; Metabolic engineering; Synthetic biology; Terpenes

Indexed keywords

BIOSYNTHESIS; DISEASE CONTROL; HYDROCARBONS; METABOLITES; ONCOLOGY;

ARTEMISININ; ISOPRENOIDS; METABOLIC ENGINEERING; SYNTHETIC BIOLOGY; TERPENES;

MOLECULAR DYNAMICS;

3 CARENE; 8 EPICEDROL; AMORPHA 4,11 DIENE; ARISTOLOCHENE; ARTEMISIN; DELTA CADINENE; DITERPENE; ISOPRENOID; LINALOOL; MEVALONIC ACID; PACLITAXEL; SESQUITERPENE; TAXA 4(5),11(12) DIENE; TAXADIEN 5ALPHA ACETOXY 10BETA OL; TERPENE; TERPENOID DERIVATIVE; VETISPIRADIENE;

BIOENGINEERING; CANCER; DRUG; ISOPRENOID; SECONDARY METABOLITE; TERPENE;

ARABIDOPSIS; BIOENGINEERING; BIOSYNTHESIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ECOLOGY; NONHUMAN; SHORT SURVEY; TOBACCO;

ARTEMISININS; GENETIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; PACLITAXEL; SESQUITERPENES; TERPENES;

EID: 33845736982     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-006-0593-1     Document Type: Short Survey

References (78)

1. Aharoni A, Giri AP et al (2003) Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. Plant Cell 15:2866-2884
2. Aubourg S, Lecharny A et al (2002) Genomic analysis of the terpenoid synthase (AtTPS) gene family of Arabidopsis thaliana. Mol Genet Genomics 267:730-745
3. Back K, Chappell J (1995) Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases. J Biol Chem 270:7375-7381
4. Back K, Chappell J (1996) Identifying functional domains within terpene cyclases using a domain-swapping strategy. Proc Natl Acad Sci USA 93:6841-6845
5. Back K, Nah J et al (2000) Cloning of a sesquiterpene cyclase and its functional expression by domain swapping strategy. Mol Cell 10:220-225
6. Barkovich R, Liao JC (2001) Metabolic engineering of isoprenoids. Metab Eng 3:27-39
7. Bertea CM, Freije JR et al (2005) Identification of intermediates and enzymes involved in the early steps of artemisinin biosynthesis in Artemisia annua. Planta Med 71:40-47
8. Besumbes O, Sauret-Gueto S et al (2004) Metabolic engineering of isoprenoid biosynthesis in Arabidopsis for the production of taxadiene, the first committed precursor of Taxol. Biotechnol Bioeng 88:168-175
9. Caruthers JM, Kang I et al (2000) Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti. J Biol Chem 275:25533-25539
10. Chen XY, Chen Y et al (1995) Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis. Arch Biochem Biophys 324:255-266
11. Colby SM, Crock J et al (1998) Germacrene C synthase from Lycopersicon esculentum cv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Proc Natl Acad Sci USA 95:2216-2221
12. Davis EM, Croteau R (2000) Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes. Top Curr Chem 209:53-95
13. Dejong JM, Liu Y et al (2006) Genetic engineering of taxol biosynthetic genes in Saccharomyces cerevisiae. Biotechnol Bioeng 93:212-224
14. Dictionary of natural products (2004) Version 8.1 (HRD), 1st edn. Chapman & Hall, London, UK
15. Facchini PJ, Chappell J (1992) Gene family for an elicitor-induced sesquiterpene cyclase in tobacco. Proc Natl Acad Sci USA 89:11088-11092
16. Faldt J, Arimura G et al (2003) Functional identification of AtTPS03 as (E)-beta-ocimene synthase: a monoterpene synthase catalyzing jasmonate-and wound-induced volatile formation in Arabidopsis thaliana. Planta 216:745-751
17. Fleet CM, Yamaguchi S et al (2003) Overexpression of AtCPS and AtKS in Arabidopsis confers increased ent-kaurene production but no increase in bioactive gibberellins. Plant Physiol 132:830-839
18. Friesen JA, Rodwell VW (2004) The 3-hydroxy-3-methylglutaryl coenzyme-A (HMG-CoA) reductases. Genome Biol 5:248
19. Grochowski LL, Xu H et al (2006) Methanocaldococcus jannaschii uses a modified mevalonate pathway for biosynthesis of isopentenyl diphosphate. J Bacteriol 188:3192-3198
20. Hahn FM, Hurlburt AP et al (1999) Escherichia coli open reading frame 696 is idi, a nonessential gene encoding isopentenyl diphosphate isomerase. J Bacteriol 181:4499-4504
21. Hamano Y, Kuzuyama T et al (2002) Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin. J Biol Chem 277:37098-37104
22. Hecht S, Eisenreich W et al (2001) Studies on the nonmevalonate pathway to terpenes: the role of the GcpE (IspG) protein. Proc Natl Acad Sci USA 98:14837-14842
23. Hefner J, Rubenstein SM et al (1996) Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis. Chem Biol 3:479-489
24. Hefner J, Ketchum RE et al (1998) Cloning and functional expression of a cDNA encoding geranylgeranyl diphosphate synthase from Taxus canadensis and assessment of the role of this prenyltransferase in cells induced for taxol production. Arch Biochem Biophys 360:62-74
25. Hezari M, Lewis NG et al (1995) Purification and characterization of taxa-4(5),11(12)-diene synthase from pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis. Arch Biochem Biophys 322:437-444
26. Hilker M, Kobs C et al (2002) Insect egg deposition induces Pinus sylvestris to attract egg parasitoids. J Exp Biol 205:455-461
27. Hohn TM, Ohlrogge JB (1991) Expression of a fungal sesquiterpene cyclase gene in transgenic tobacco. Plant Physiol 97:460-462
28. Horiguchi T, Rithner CD et al (2002) Studies on taxol biosynthesis. Preparation of taxa-4(20),11(12)-dien-5 alpha-acetoxy-10 beta-ol by deoxygenation of a taxadiene tetraacetate obtained from Japanese yew. J Org Chem 67:4901-4903
29. Huang Q, Roessner CA et al (2001) Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorg Med Chem 9:2237-2242
30. Jennewein S, Rithner CD et al (2003) Taxoid metabolism: taxoid 14beta-hydroxylase is a cytochrome P450-dependent monooxygenase. Arch Biochem Biophys 413:262-270
31. Jennewein S, Long RM et al (2004) Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis. Chem Biol 11:379-387
32. Kappers IF, Aharoni A et al (2005) Genetic engineering of terpenoid metabolism attracts bodyguards to Arabidopsis. Science 309:2070-2072
33. Kuzma J, Nemecek-Marshall M et al (1995) Bacteria produce the volatile hydrocarbon isoprene. Curr Microbiol 30:97-103
34. Lange BM, Croteau R (1999a) Genetic engineering of essential oil production in mint. Curr Opin Plant Biol 2:139-144
35. Lange BM, Croteau R (1999b) Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: cloning and heterologous expression of 1-deoxy-D-xylulose-5-phosphate reductoisomerase from peppermint. Arch Biochem Biophys 365:170-174
36. Lange BM, Wildung MR et al (2000) Probing essential oil biosynthesis and secretion by functional evaluation of expressed sequence tags from mint glandular trichomes. Proc Natl Acad Sci USA 97:2934-2939
37. Lesburg CA, Zhai G et al (1997) Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science 277:1820-1824
38. Lesburg CA, Caruthers JM et al (1998) Managing and manipulating carbocations in biology: terpenoid cyclase structure and mechanism. Curr Opin Struct Biol 8:695-703
39. Little DB, Croteau RB (2002) Alteration of product formation by directed mutagenesis and truncation of the multiple-product sesquiterpene synthases delta-selinene synthase and gamma-humulene synthase. Arch Biochem Biophys 402:120-235
40. Lucker J, Schwab W et al (2004) Metabolic engineering of monoterpene biosynthesis: two-step production of (+)-transisopiperitenol by tobacco. Plant J 39:135-145
41. Luttgen H, Rohdich F et al (2000) Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Proc Natl Acad Sci USA 97:1062-1067
42. Mahmoud SS, Croteau RB (2001) Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase. Proc Natl Acad Sci USA 98:8915-8920
43. Mahmoud SS, Croteau RB (2003) Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Proc Natl Acad Sci USA 100:14481-14486
44. Martin VJ, Yoshikuni Y et al (2001) The in vivo synthesis of plant sesquiterpenes by Escherichia coli. Biotechnol Bioeng 75:497-503
45. Martin VJ, Pitera DJ et al (2003) Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol 21:796-802
46. Mercke P, Crock J et al (1999) Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L. Arch Biochem Biophys 369:213-222
47. Mercke P, Bengtsson M et al (2000) Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L. Arch Biochem Biophys 381:173-180
48. Nakano C, Okamura T et al (2005) Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton. Chem Commun (Camb) 8:1016-1018
49. Ohnuma SI, Nakazawa T et al (1996a) Conversion from farnesyl diphosphate synthase to geranylgeranyl diphosphate synthase by random chemical mutagenesis. J Biol Chem 271:10087-10095
50. Ohnuma SI, Narita K et al (1996b) A role of the amino acid residue located on the fifth position before the first aspartate-rich motif of farnesyl diphosphate synthase on determination of the final product. J Biol Chem 271:30748-30754
51. Rasmann S, Kollner TG et al (2005) Recruitment of entomopathogenic nematodes by insect-damaged maize roots. Nature 434:732-737
52. Reiling KK, Yoshikuni Y et al (2004) Mono and diterpene production in Escherichia coli. Biotechnol Bioeng 87:200-212
53. Ro DK, Paradise EM et al (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440:940-943
54. Rodriguez-Concepcion M (2004) The MEP pathway: a new target for the development of herbicides, antibiotics and antimalarial drugs. Curr Pharm Des 10:2391-2400
55. Rohdich F, Wungsintaweekul J et al (1999) Cytidine 5′-triphosphate- dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol. Proc Natl Acad Sci USA 96:11758-11763
56. Rohdich F, Hecht S et al (2002) Studies on the nonmevalonate terpene biosynthetic pathway: metabolic role of IspH (LytB) protein. Proc Natl Acad Sci USA 99:1158-1163
57. Rohmer M, Knani M et al (1993) Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J 295(Pt 2):517-524
58. Roth RJ, Acton N (1989) A simple conversion of artemisinic acid into artemisinin. J Nat Prod 52:1183-1185
59. Rynkiewicz MJ, Cane DE et al (2001) Structure of trichodiene synthase from Fusarium sporotrichioides provides mechanistic inferences on the terpene cyclization cascade. Proc Natl Acad Sci USA 98:13543-13548
60. Rynkiewicz MJ, Cane DE et al (2002) X-ray crystal structures of D100E trichodiene synthase and its pyrophosphate complex reveal the basis for terpene product diversity. Biochemistry 41:1732-1741
61. Smit A, Mushegian A (2000) Biosynthesis of isoprenoids via mevalonate in Archaea: the lost pathway. Genome Res 10:1468-1484
62. Starks CM, Back K et al (1997) Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science 277:1815-1820
63. Steele CL, Crock J et al (1998a) Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase. J Biol Chem 273:2078-2089
64. Steele CL, Katoh S et al (1998b) Regulation of oleoresinosis in grand fir (Abies grandis): differential transcriptional control of monoterpene, sesquiterpene, and diterpene synthase genes in responses to wounding. Plant Physiol 116:1497-1504
65. Szkopinska A, Swiezewska E et al (2000) The regulation of activity of main mevalonic acid pathway enzymes: farnesyl diphosphate synthase, 3-hydroxy-3-methylglutaryl-CoA reductase, and squalene synthase in yeast Saccharomyces cerevisiae. Biochem Biophys Res Commun 267:473-477
66. Takahashi S, Kuzuyama T et al (1998) A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis. Proc Natl Acad Sci USA 95:9879-9884
67. Tarshis LC, Yan M et al (1994) Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution. Biochemistry 33:10871-10877
68. Tholl D, Chen F et al (2005) Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers. Plant J 42:757-771
69. Umeno D, Tobias AV et al (2005) Diversifying carotenoid biosyntheticpathways by directed evolution. Microbiol Mol Biol Rev 69:51-78
70. Veen M, Lang C (2004) Production of lipid compounds in the yeast Saccharomyces cerevisiae. Appl Microbiol Biotechnol 63:635-646
71. Vogel BS, Wildung MR et al (1996) Abietadiene synthase from grand fir (Abies grandis): cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis. J Biol Chem 271:23262-23268
72. Walker K, Ketchum REB et al (1999) Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis. Arch Biochem Biophys 364:273-279
73. Wallaart TE, Bouwmeester HJ et al (2001) Amorpha-4,11-diene synthase: cloning and functional expression of a key enzyme in the biosynthetic pathway of the novel antimalarial drug artemisinin. Planta 212:460-465
74. Wildung MR, Croteau R (1996) A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. J Biol Chem 271:9201-9204
75. Williams DC, Carroll BJ et al (2000) Intramolecular proton transfer in the cyclization of geranylgeranyl diphosphate to the taxadiene precursor of taxol catalyzed by recombinant taxadiene synthase. Chem Biol 7:969-977
76. Yang D, Shipman LW et al (2002) Structure of the Methanococcus jannaschii mevalonate kinase, a member of the GHMP kinase superfamily. J Biol Chem 277:9462-9467
77. Yoshikuni Y, Ferrin TE et al (2006) Designed divergent evolution of enzyme function. Nature 440:1078-1082
78. Yoshioka H, Yamada N et al (1999) cDNA cloning of sesquiterpene cyclase and squalene synthase, and expression of the genes in potato tuber infected with Phytophthora infestans. Plant Cell Physiol 40:993-998