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Cytochrome P450S and Uses Thereof Joe Chappell University of Kentucky, [email protected]

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Cytochrome P450S and Uses Thereof Joe Chappell University of Kentucky, Chappell@Uky.Edu University of Kentucky UKnowledge Plant and Soil Sciences Faculty Patents Plant and Soil Sciences 5-13-2014 Cytochrome P450S and Uses Thereof Joe Chappell University of Kentucky, [email protected] Lyle F. Ralston Right click to open a feedback form in a new tab to let us know how this document benefits oy u. Follow this and additional works at: https://uknowledge.uky.edu/pss_patents Part of the Plant Sciences Commons Recommended Citation Chappell, Joe and Ralston, Lyle F., "Cytochrome P450S and Uses Thereof" (2014). Plant and Soil Sciences Faculty Patents. 16. https://uknowledge.uky.edu/pss_patents/16 This Patent is brought to you for free and open access by the Plant and Soil Sciences at UKnowledge. It has been accepted for inclusion in Plant and Soil Sciences Faculty Patents by an authorized administrator of UKnowledge. For more information, please contact [email protected]. USOO8722363B2 (12) United States Patent (10) Patent N0.2 US 8,722,363 B2 Chappell et a]. (45) Date of Patent: *May 13, 2014 (54) CYTOCHROME P450S AND USES THEREOF 6,531,303 B1 3/2003 Millis et a1. ................. .. 435/155 6,559,297 B2 5/2003 Chappellet a1. .. 536/23.1 ~ . ~ 6,569,656 B2 5/2003 Chappellet a1. .. .. 435/183 (n)A”mmtu%ER$mm&Mmm@m QMWQB21MW3Qm?MAH “Mw? . 6,689,593 B2 2/2004 Millis et al. .. 435/155 (72) Inventors: Joseph Chappell,~Lex1ngton, KY (US); 6,890,752 B2 500% chappenet 31‘ u N 435625 Lyle F. Ralston, Sao Paulo (BR) 7,186,891 B1 3/2007 Chappell et a1. .. .. 800/298 7,405,057 B2* 7/2008 Chappellet a1. .. 435/69.1 (73) Assignee: University of Kentucky Research 9141313611? 31~ ~~ ~ 5536655332? - - , , u 1en e a . ..... .. .. Foundatlon’ Lexmgton’ KY (Us) 8,106,260 B2 1/2012 Chappelletal. .. .. 800/298 8,124,811 B2 2/2012 J l' t l. ..... .. .. 568/367 ( * ) Notice: Subject to any disclaimer, the term ofthis 8,192,950 B2 @2012 6111;123:112 31‘ n 435/41 patent 1s extended or adjusted under 35 8,263,362 B2* 9/2012 Chappellet a1. .. 435/69.1 Lrsx3.154(h)hy()days. 8354504 B2 02013 (happenetm... n 530679 _ _ _ _ _ 8362309 B2 02013 Juhenetal.n ..583B60 Th1s patent 1s 511131601 to a term1nal d1s- 8,445,231 B2* 5/2013 Chappellet a1. 435/69.1 Claimer_ 8,481,286 B2 7/2013 Julien etal. 435/69.1 2003/0166255 A1 9/2003 Chappell ..... .. .. 435/252.3 _ 2004/0078840 A1 4/2004 Chappellet a1. .. .. 800/278 (21) APPI'NO" 13/986’446 2006/0218661 A1 9/2006 Chappelletal. .. .. 800/278 _ 2007/0231861 A1 10/2007 Millis et al. 435/69.1 Q3 Fm?l WhylZM3 mmmmmwim 10mm Mmmmmnu “m4unm 2007/0238159 A1 10/2007 Millis et al. 435/252.33 (65) Prior Publication Data 2007/0238160 A1 10/2007 Millis et al. 435/252.33 2007/0254354 A1 11/2007 Millis et al. ............ .. 435/252.33 US 2013/0330793 A1 Dec. 12, 2013 . (Cont1nued) (63) Continuation of application No. 13/ 199,349, ?led on / Aug. 26, 2011, HOW Pat. No. 8,445,231, which is a {50 Zooggs/éégg‘; I? continuation of application No. 12/ 182,000, ?led on I Jul. 29, 2008, HOW Pat. No. 8,263,362, which is a (Commued) continuation of application No. 10/097,559, ?led on OTHER PUBLICATIONS Mar. 8, 2002, now Pat. No. 7,405,057. International Search Report, issued Dec. 17, 2002, in connection With (60) Provisional application No. 60/274,421, ?led on Mar. 9, 2001, provisional application No. 60/275,597, ?led corresponding International Patent Application No. PCT/US02/ on Mar. 13,2001. 06912, 4 pages. International Preliminary Examination Report, issued Apr. 24, 2003, (51) Int. Cl. in connection With corresponding International Patent Application No. PCT/US02/06912, 4 pages. C12N1/00 (2006.01) Partial European Search Report, issued Jun. 16, 2004, in connection C12N1/06 (2006.01) With corresponding European Patent Application No. 027097971, 7 C12N 5/00 (2006.01) pages. C12N 5/07 (2010.01) Of?ce Action, issued Jul. 1, 2004, in connection With corresponding (52) US. Cl. U.S. Appl. No. 10/097,559, 10 pages. USPC ..... .. 435/69.1; 435/468; 435/348; 435/252.1; Supplemental European Search Report, issued Sep. 8, 2004, in con 435/252.2; 435/155; 435/419 nection With corresponding European Patent Application No. (58) Field of Classi?cation Search 027097971, 6 pages. None See application ?le for complete search history. (Continued) (56) References Cited Primary Examiner * Medina A Ibrahim (74) Attorney, Agent, 0rFirm * McKenna Long &Aldridge U.S. PATENT DOCUMENTS LLP; Stephanie Seidman 5,589,619 A 12/1996 Chappell et a1. ............ .. 800/205 (57) ABSTRACT 5,672,487 A 9/1997 Schweden et a1. .. .. 435/69.1 5,741,674 A 4/1998 Schweden et a1. .. .. 435/69.1 The invention features isolated cytochrome P450 polypep 5,766,911 A 6/1998 Koike et a1. 435/193 tides and nucleic acid molecules, as well as expression vec 5,824,774 A 10/1998 Chappell et a1. 530/350 tors and transgenic plants containing these molecules. In 5,981,843 A 11/1999 Chappell et a1. 800/301 5,994,114 A 11/1999 Croteau et a1. .. 435/232 addition, the invention features uses of such molecules in 6,072,045 A 6/2000 Chappell et a1. .. 536/23.1 methods of increasing the level of resistance against a disease 6,100,451 A 8/2000 Chappell et a1. 800/298 caused by a plant pathogen in a transgenic plant, in methods 6,117,649 A 9/2000 Bellamine et a1. ............ .. 435/25 for producing altered compounds, for example, hydroxylated 6,194,185 B1 2/2001 Croteau et a1. .............. .. 435/189 compounds, and in methods of producing isoprenoid com 6,331,660 B1 12/2001 Chomet et a1. .. 800/278 6,368,837 B1 4/2002 Gatenby et a1. 435/146 pounds. 6,468,772 B1 10/2002 Chappell et a1. 435/183 6,495,354 B2 12/2002 Chappell et a1. ............ .. 435/183 29 Claims, 11 Drawing Sheets US 8,722,363 B2 Page 2 (56) References Cited Examination Report, issued Nov. 20, 2012, and received Nov. 23, 2012, in connection With corresponding Canadian Patent Application U.S. PATENT DOCUMENTS No. 2,440,278, 7 pages. Akiyoshi-Shibata et al., “Further oxidation of hydroxycalcidiol by 2008/0178354 A1 7/2008 Chappell et al. ............ .. 800/298 calcidiol 24 -hydroxylase. A study With the mature enzyme expressed 2008/0233622 A1 9/2008 Julien et al. 435/148 in Escherichia coli,” Eur. J. Biochem. 224:335-343 (1994). 2010/0035329 A1 2/2010 Millis et al. .............. .. 435/254.2 Allylix, “Protein engineering and chembiosynthesis to produce novel 2010/0120110 A1 5/2010 Chappell ..................... .. 435/166 sesquiterpenoids,” Presentation at BIO World Congress on Industrial 2010/0129306 A1 5/2010 Julien et al. 424/65 2010/0151519 A1 6/2010 Julien et al. 435/69.1 Biotechnology & Bioprocessing, Washington, DC, Jun. 28, 2010, 2010/0151555 A1 6/2010 Julien etal. 435/193 19 pages. 2010/0216186 A1 8/2010 Chappellet al. 435/69.1 An et al., “Functional analysis of the 3‘ control region of the potato 2011/0081703 A1 4/2011 Chappellet al. 435/193 wound-inducible proteinase inhibitor II gene,” Plant Cell 1:115-122 2011/0318797 A1 12/2011 Chappellet al. 435/155 (1989). 2012/0129235 A1 5/2012 Julien et al. 435/166 An et al., “Organ-speci?c and developmental regulation of the 2012/0196340 A1 8/2012 Chappellet al. ............ .. 435/148 nopaline synthase promoter in transgenic tobacco plants,” Plant 2013/0071877 A1 3/2013 Chappellet al. .............. .. 435/41 Physiol. 88:547-552 (1988). 2013/0122560 A1 5/2013 Julien et al. 435/148 Andersson et al., “Physiology and molecular genetics of 17 beta 2013/0236943 A1 9/2013 Julien et al. ................. .. 435/166 hydroxysteroid dehydrogenases,” Steroids 62(1): 143-147 (1997). Back et al., “Cloning and bacterial expression of sesquiterpene FOREIGN PATENT DOCUMENTS cyclase, a key branch point enzyme for the synthesis of sesquiterpenoid phytoalexin capsidiol in UV-challenged leaves of W0 WO 97/37664 10/1997 Capsicum annuum,” Plant Cell. Physiol. 39:899-904 (1998). W0 WO 97/38571 10/1997 Back et al., “Expression of a plant sesquiterpene cyclase gene in W0 WO 97/38703 10/1997 W0 WO 00/17327 3/2000 Escherichia coli,” Arch. Biochem. Biophys. 315:527-532 (1994). W0 W0 02/072758 9/2002 Back et al., “Cloning and bacterial expression of a sesquiterpene W0 WO 2010/019696 2/2010 cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases,” J. Biol. Chem. 270:7375-7381 (1995). OTHER PUBLICATIONS Back et al., “Identifying functional domains Within terpene cyclases Examination Report, issued Sep. 19, 2005, in connection With cor using a domain-swapping strategy,” Proc. Natl. Acad. Sci. USA. responding European Patent Application No. 02709797.1, 6 pages. 93:6841-6845 (1996). Response to Examination Report, ?led Feb. 9, 2006, in connection Beckman et al., “Human 25-hydroxyvitamin D3 -24-hydroxylase, a With corresponding European Patent Application No. 02709797, 11 multicatalytic enzyme,” Biochem. 35:8465-8472 (1996). pages. Boddupalli et al., “Fatty acid monooxygenation by P450BM-3: prod Of?ce Action, issued Mar. 13, 2006, in connection With correspond uct identi?cation and proposed mechanisms for the sequential ing U.S. Appl. No. 10/097,559, 9 pages. hydroxylation reactions,” Arch. Biochem. Biophys. 292:20-28 Of?ce Action, issued Oct. 12, 2006, in connection With correspond (1992). ing U.S. Appl. No. 10/097,559, 12 pages. Bozak et al., “Sequence analysis of ripening-related cytochrome Of?ce Action, issued May 1, 2007, in connection With corresponding P-450 cDNAs from avocado fruit,” Proc.
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