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(12) United States Patent (10) Patent No.: US 8.263,362 B2 Chappell Et Al

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(12) United States Patent (10) Patent No.: US 8.263,362 B2 Chappell Et Al US008263362B2 (12) United States Patent (10) Patent No.: US 8.263,362 B2 Chappell et al. (45) Date of Patent: *Sep. 11, 2012 (54) CYTOCHROME P450S AND USES THEREOF 2003,0166255 A1 9/2003 Chappell .................... 435/252.3 2004f0078840 A1 4/2004 Chappellet al. .. 800,278 2006/0218661 A1 9/2006 Chappell et al. .. 800,278 (75) Inventors: Joseph Chappell, Lexington, KY (US); 2007/0231861 A1 10/2007 Millis et al. ... 435/69.1 Lyle F. Ralston, Kirkwood, MO (US) 2007/0238157 A1 10/2007 Millis et al. ... ... 435,166 2007/0238159 A1 10/2007 Millis et al. ... 435/252.33 (73) Assignee: University of Kentucky Research 2007/02381.60 A1 10/2007 Millis et al. ... 435/252.33 Foundation, Lexington, KY (US) 2007/0254354 A1 11/2007 Millis et al. ... 435/252.33 2008. O178354 A1 7/2008 Chappellet al. .............. 800,298 2008, 0233622 A1 9, 2008 Julien et al. ... ... 435,148 (*) Notice: Subject to any disclaimer, the term of this 2010.0035329 A1 2/2010 Millis et al. ... ... 435,254.2 patent is extended or adjusted under 35 2010, O151519 A1 6/2010 Julien et al. ... ... 435/69.1 U.S.C. 154(b) by 32 days. 2010. O151555 A1 6/2010 Julien et al. ... 435/193 2010/0216186 A1 8/2010 Chappellet al. .. 435/69.1 This patent is Subject to a terminal dis 2011/0081703 A1 4/2011 Chappell et al. .............. 435/193 claimer. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 12/182,000 JP 2000-511404 9, 2000 WO 96.36697 11, 1996 WO 97,385.71 10, 1997 (22) Filed: Jul. 29, 2008 WO 97,387O3 10, 1997 WO WO97,37664 10, 1997 (65) Prior Publication Data WO OO/17327 3, 2000 WO O2/O72758 9, 2002 US 2010/O12O11.0 A1 May 13, 2010 WO 2010/019696 2, 2010 Related U.S. Application Data OTHER PUBLICATIONS Walker & Croteau, “Molecular Cloning of a 10-deacetylbaccatin (63) Continuation of application No. 10/097.559, filed on III-10-O-acetyl Transferase cDNA from Taxus and Functional Mar. 8, 2002, now Pat. No. 7,405,057. Expression in Escherichia coli.” Jan. 18, 2000,97(2):583-587. Back et al., “Expression of a Plant Sesquiterpene Cyclase Gene in (60) Provisional application No. 60/274,421, filed on Mar. Escherichia coli.” Archives in Biochemistry and Biophysics (1994) 9, 2001, provisional application No. 60/275,597, filed 315:527-532. on Mar. 13, 2001. Mandujano-Chavez et al., “Differential Induction of Sesquiterpene Metabolism in Tobacco Cell Suspension Cultures by Methyl (51) Int. Cl. Jasmonate and Fungal Elicitor.” Archives in Biochemistry and Bio CI2N I/00 (2006.01) physics (2000) 381:285-294. CI2N I/06 (2006.01) Ralston et al... “Cloning. Heterologous Expression, and Functional Characterization of 5-epi-aristolochene-1,3-Dihydroxylase from CI2N5/00 (2006.01) Tobacco (Nicotiana tobacum), "Archives in Biochemistry and Bio CI2N 5/07 (2010.01) physics (2001) 393:222-235. (52) U.S. Cl. ... 435/69.1; 435/419; 435/348; 435/252.1; Zook et al., “Characterization of Novel Sesquiterpene Biosynthesis 435/252.2 in Tobacco Expressing Fungal Sesquiterpenoid Synthase. Plant Physiology (1996) 112:311-318. (58) Field of Classification Search ........................ None Akiyoshi-Shibata et al., “Further Oxidation of Hydroxycalcidiol by See application file for complete search history. Calcidiol 24-Hydroxylase. A Study with the Mature Enzyme Expressed in Escherichia coli.” Eur, J. Biochem. (1994) 224:335 (56) References Cited 343. Back & Chappell, “Cloning and Bacterial Expression of a U.S. PATENT DOCUMENTS Sesquiterpene Cyclase from Hyoscyamus multicus and its Molecular 5,589,619 A 12/1996 Chappell et al. .............. 800,205 Comparison to Related Terpene Cyclases,” J. Biol. Chem. (1995) 5,672.487 A 9, 1997 Schweden et al. 27O:7375-7381. 5,741,674. A 4, 1998 Schweden et al. Back & Chappell, “Identifying Functional Domains within Terpene 5,766,911 A 6, 1998 Koike et al. ................... 435/193 Cyclases Using a Domain-Swapping Strategy.” Proc. Natl. Acad. Sci. 5,824,774 A 10/1998 Chappell et al. U.S.A. (1996) 93:6841-6845. 5,981,843. A 11/1999 Chappell et al. .............. 800/301 5,994,114 A 11/1999 Croteau et al. ................ 435/232 (Continued) 6,072,045 A 6/2000 Chappell et al. Primary Examiner — Medina AIbrahim 6,100.451 A 8/2000 Chappell et al. .............. 800,298 6,117,649 A 9, 2000 Bellamine et al. (74) Attorney, Agent, or Firm — McKenna Long & Aldridge 6,194,185 B1 2, 2001 Croteau et al. LLP; Stephanie Seidman 6,331,660 B1 12/2001 Chomet et al. (57) ABSTRACT 6,368,837 B1 4/2002 Gatenby et al. 6,468,772 B1 10/2002 Chappell et al. .............. 435/183 The invention features isolated cytochrome P450 polypep 6,495,354 B2 12/2002 Chappell et al. ... 435/183 tides and nucleic acid molecules, as well as expression vec 6,531,303 B1 3/2003 Millis et al. ..... 435/155 tors and transgenic plants containing these molecules. In 6,559,297 B2 5/2003 Chappell et al. 536,23.1 addition, the invention features uses of Such molecules in 6,569,656 B2 5/2003 Chappell et al. ... 435/183 6,645,762 B2 11/2003 Chappell et al. 435/325 methods of increasing the level of resistance against a disease 6,689,593 B2 2/2004 Millis et al. ..... 435/155 caused by a plant pathogen in a transgenic plant, in methods 6,890,752 B2 5/2005 Chappell et al. 435/325 for producing altered compounds, for example, hydroxylated 7,186,891 B1 3/2007 Chappell et al. ... 800,298 compounds, and in methods of producing isoprenoid com 7,405,057 B2 * 7/2008 Chappell et al. ... 435/69.1 pounds. 7,442,785 B2 10/2008 Chappell et al. 536,236 7.622,614 B2 11/2009 Julien et al. ................... 568.327 20 Claims, 11 Drawing Sheets US 8,263,362 B2 Page 2 OTHER PUBLICATIONS Hutvagner et al., “Isolation and Sequence Analysis of a cDNA and a Back et al., “Cloning and Bacterial Expression of Sesquiterpene Related Gene for Cytochrome P450 Proteins from Solanum Cyclase, a Key Branch Point Enzyme for the Synthesis of chacoense.” Gene (1998) 188:247-252. Sesquiterpenoid Phytoalexin Capsidiol in UV-Challenged Leaves of Keller et al., "Sesquiterpene Cyclase Is not a Determining Factor for Capsicum annuum.” Plant Cell Physiol. (1998) 39:899-904. Elicitor- and Pathogen-Induced Capsidiol Accumulation in Beckman et al., “Human 25-Hydroxyvitamin D3-24-Hydroxylase, a Tobacco.” Planta (1998) 205:467-476. Multicatalytic Enzyme.” Biochemistry (1996) 35:8465-8472. Lupien et al., “Regiospecific Cytochrome P450 Limonene Boddupalli et al., “Fatty Acid Monooxygenation by P450BM-3: Hydroxylases from Mint (Mentha) Species: cDNA Isolation, Char Product Identification and Proposed Mechanisms for the Sequential acterization, and Functional Expression of (-)-4S-Limonene-3- Hydroxylation Reactions.” Arch. Biochem. Biophys. (1992) 292:20 Hydroxylase and (-)-4S-Limonene-6-Hydroxylase.” Arch. 28. Chappellet al., "Accumulation of Capsidiol in Tobacco Cell Cultures Biochem. Biophys. (1999) 368:181-192. Treated with Fungal Elicitor.” Phytochemistry (1987) 26:2259-2260. Mandujano-Chavez et al., “Differential Induction of Sesquiterpene Chappell & Nable, “Induction of Sesquiterpenoid Biosynthesis in Metabolism in Tobacco Cell Suspension Cultures by Methyl Tobacco Cell Suspension Cultures by Fungal Elicitor.” Plant Physiol. Jasmonate and Fungal Elicitor.” Arch. Biochem. Biophys. (2000) (1987) 85:469-473. 381:285-294. Chappell, “Biochemistry and Molecular Biology of the Isoprenoid Mathis et al., “Pre-Steady-State Study of Recombinant Biosynthetic Pathway in Plants.” Annu. Rev. Plant Physiol. Plant Sesquiterpene Cyclases.” Biochemistry (1997) 36:8340-8348. Mol. Biol. (1995) 46:521-547. Maughan et al., “Expression of CYP71B7, a Cytochrome P450 Chapple, “Molecular-Genetic Analysis of Plant Cytochrome P450 Expressed Sequence Tag from Arabidopsis thaliana. Arch. Dependent Monooxygenases.” Annu. Rev. Plant Physiol. Plant Mol. Biochem. Biophys. (1997) 341:104-111. Biol. (1998) 49:311-343. Milet et al., “Capsidiol and Ethylene Production by Tobacco Cells in Clarket al., “Spatially Distinct Expression of Two New Cytochrome Response to Cryptogein, an Elicitor from Phytophthora cryptogea, P450s in Leaves of Nepeta racemosa: Identification of a Trichome Phytochemistry (1991) 30:2171-2173. Specific Isoform.” Plant Mol. Biol. (1997) 33:875-885. Miller, "Structure of Genes Encoding Steriodogenic Enzymes,” J. Coolbaugh et al., “Studies on the Specificity and Site of Action of a Steroid. Biochem. (1987) 27:759-766. alpha-Cyclopropyl-alpha-p-Methoxphenyl-5-Pyrimidine Methyl Molotet al., “Relations Between Capsidiol Concentration, Speed of Alcohol Amcymidol), a Plant Growth Regulator.” Plant Physiol. Fungal Invasion and Level of Induced Resistance in Cultivars of (1978) 62:571-576. Pepper (Capsicum annuum) Susceptible or Resistant to Cooper & Porter, "Mutagenicity of Nitrosamines in Methyltransferase-Deficient Strains of Salmonella typhimurium Phytophthora capsici.” Physiol. Plant Pathol. (1981) 18:379-389. Coexpressing Human Cytochrome P4502E1 and Reductase.” Mutat. Nedelkina et al., “Novel Characteristics and Regulation of a Diver Res. (2000) 454:45-52. gent Cinnamate 4-Hydroxylase (CYP3A15) from French Bean: Dieneret al., “Sterol Methyltransferase 1 Controls the Level of Cho Engineering Expression in Yeast.” Plant Mol. Biol. (1999) 39:1079 lesterol in Plants.” Plant Cell (2000) 12:853-870. 1090. Dietz et al., “Nucleotide Sequences of Subunit E of the Vacuolar O'Donohue et al., “Chemical Synthesis, Expression and Proton-ATPase of Spinacia oleracea (Accession No. X96785) and Mutagenesis of a Gene Encoding beta-Cryptogein, an Elicitin Pro Arabidopsis thaliana (Accession No. X921117).” (Plant Gene Reg duced by Phytophthora cryptogea.” Plant Mol. Biol. (1995) 27:577 ister PGR 96-037) Plant Physiol. (1996) 111:652. 586. Dong & Porter, "Coexpression of Mammalian Cytochrome P450 and O'Keefe & Leto, “Cytochrome P-450 from the Mesocarp of Avocado Reductase in Escherichia coli.” Arch. Biochem. Biophys. (1996) (Persea americana).” Plant Physiol.
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