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United States Patent (19) 11 Patent Number: 5,871,988 Croteau Et Al

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United States Patent (19) 11 Patent Number: 5,871,988 Croteau Et Al USOO5871988A United States Patent (19) 11 Patent Number: 5,871,988 Croteau et al. (45) Date of Patent: Feb. 16, 1999 54) DNA ENCODING LIMONENE SYNTHASE Alberts, B. et al. “Molecular Biology of the Cell” published FROM MENTHA SPICATA 1989 by Garland Publishing Inc. (N.Y.), pp. 262-263. Alberts, B. et al. (1989) Molecular Biology of the Cell 75 Inventors: Rodney B. Croteau, Pullman, Wash.; Second Ed. Garland Publishing Inc., New York. pp. 185-187 Shelia M. Colby, Berkeley, Calif. and 265-266. Colby, S.M., Alonso, W.R., Croteau, R. (1992) “Isolation 73 Assignee: Washington State University Research and characterization of cDNA encoding limonene cyclase in Foundation, Pullman, Wash. spearmint J. Cell Biochem. Suppl. 0 vol. 16, Part F. p. 230. 21 Appl. No.: 846,526 Primary Examiner Robert A. Wax 22 Filed: Apr. 29, 1997 ASSistant Examiner Kawai Lau Attorney, Agent, or Firm-Christensen O'Connor Johnson Related U.S. Application Data & Kindness PLLC 57 ABSTRACT 63 Continuation of Ser. No. 582,802, Jan. 4, 1996, abandoned, which is a continuation of Ser. No. 145,941, Oct. 28, 1993, cDNA encoding (-)-4S-limonene Synthase from Spearmint abandoned. has been isolated and Sequenced, and the corresponding 51) Int. Cl. ............................. C12N 9/00; C12N 15/63; amino acid Sequence has been determined. Accordingly, C12P 21/02; CO7H 21/04 isolated DNA sequences are provided which code for the 52 U.S. Cl. ..................... 435/183; 435/69.1; 435/252.3; expression of limonene Synthase, Such as the Sequence 435/320.1; 536/23.2 designated SEQID No:11 which encodes limonene synthase 58 Field of Search ........................... 536/23.2; 435/183, from Spearmint (Mentha Spicata). In other aspects, repli 435/252.3, 320.1, 69.1 cable recombinant cloning vehicles are provided which code for limonene Synthase or for a base Sequence Sufficiently 56) References Cited complementary to at least a portion of the limonene Synthase DNA or RNA to enable hybridization therewith (e.g., anti PUBLICATIONS Sense limonene Synthase RNA or fragments of complemen Kang, M.H. et al. “Isolation of a genomic clone for cyto tary limonene Synthase DNA which are useful as polymerase chrome P450 oxidase from Mentha piperita” Molecules and chain reaction primerS or as probes for limonene Synthase or Cells (Sep. 1993), vol. 3, No. 3, pp. 283-288. related genes). In yet other aspects, modified host cells are Song, S.I. et al. “Molecular cloning and nucleotide Sequenc provided that have been transformed, transfected, infected ing of cDNA encoding the precursor for Soybean trypsin and/or injected with a recombinant cloning vehicle and/or inhibitor (Kunitz type)” Molecules and Cells (1991), vol. 1, DNA sequence encoding limonene Synthase. Thus, Systems No. 3, pp. 317-324, abstract only. and methods are provided for the recombinant expression of Lohman, K.N. “Floral induction in Pharbitis nil, Perilla limonene Synthase that may be used to facilitate the crispa, and Arabidopsis thaliana” Dissertation Abstracts production, isolation and purification of Significant quanti International (1992), vol.53, No. 6B, p. 2691, abstract only. ties of recombinant limonene Synthase (or of the primary The New Royal Horticultural Society Dictionary of Garden enzyme product, limonene) for Subsequent use, to obtain ing. Edited by A. Huxley et al. London: Macmillan Press, expression or enhanced expression of limonene Synthase in 1992, p. 525. plants to attain enhanced limonene production as a predator Bailey, L.H. The Standard Cyclopedia of Horticulture. New defense mechanism, or may be otherwise employed for the York: Macmillan Company, 1935, p. 2553. regulation or expression of limonene Synthase or the pro John, M.E. “An efficient method for isolation of RNA and duction of limonene. DNA from plants containing polyphenolics' Nucleic Acids Research (May, 1992), vol. 20, No. 9, p. 2381. 10 Claims, 9 Drawing Sheets N OPP SR u.(-)-Carvone -b S Geranyl (-)-4S -Limonene pyrophosphate 1N (-)-Menthol U.S Patent Feb. 16, 1999 Sheet 1 of 9 5,871,988 auoAueo-(-) ~^ |ou?uÐIN-(-) O SJSS. ?ueuouu?T-Sy-(-) auauoupiddOSS | |Áueues) æqe?dsoudouÁd U.S. Patent Feb. 16, 1999 Sheet 3 of 9 5,871,988 O 10 20 30 52. 5. Time (min.) U.S. Patent Feb. 16, 1999 Sheet 4 of 9 5,871,988 pIC5. 2 AGAGAGAGAGAGGAAGGAAAGATTAATC 28 pI C4 - 1 gagag---a------ C- - - - - - - - - - - - - - - - - pLC8.5 attaatcctagaaaaacat---a------ C- - - - - - - - - - - - - - - - - pIC5.2 ATGGCTCTCAAAGTGTTAAGTGTTGCAACTCAAATGGCGATTCCTAGCAA T 8 pLC4.1 -------------------------------------------------- pLC8.5 ------------------------ -------- - - - - - - - - - - - - - - - - - - M A Li K V L. S. V. A T Q. M. A. I. P. S. N. 17 pLC5.2 CCTAACGACATGTCTTCAACCCTCACACTTCAAATCTTCTCCAAAACTGT 128 pLC4.1 -------------------------------------------------- pLC8.5 -------------------------------------------------- L. T. T. C. L. Q. P S H E K S S P K L. L. 34 pLC5. 2 TATCTAGCACTAACAGTAGTAGTCGGTCTCGCCTCCGTGTGTATTGCTCC 178 pLC4.1 ----------------------- pLC8.5 ----------------------- pTC10. 1 C - - - - - - - - - - - - - - - - - - a- - - - - - - - - - - - - - - - - - - - - t- - - - S S T N S S S R S R L. R. V. Y. C. S. 5 O pLC5.2 TCCTCGCAACTCACTACTGAAAGACGATCCGGAAACTACAACCCTTCTCG 228 pLC10. 1. -------------------------------------------------- S. S. Q. L. T. T. E. R. R. S. G. N. Y. N P S R 67 pLC5. 2 TTGGGATGTCAACTTCATCCAATCGCTTCTCAGTGACTATAAGGAGGACA 278 pLC10.1 ------------------------- g------------------------ W. D. V N F I Q S L L S D Y K E D K 84 pILC5. 2 AACACGTGATTAGGGCTTCTGAGCTGGTCACTTTGGTGAAGATGGAACTG 328 pILC10.1 ------- H V I R A S E L V T L V K M E L 1 OO pIC5. 2 GAGAAAGAAACGGATCAAATTCGACAACTTGAGTTGATCGATGACTTGCA 378 E K E T D Q I R O L E L I D D L Q 117 pLC5. 2 GAGGATGGGGCTGTCCGATCATTTCCAAAATGAGTTCAAAGAAATCTTGT 42.8 R M G L S D H F O N E F K E I L S 134 pLC5.2 CCTCTATATATCTCGACCATCACTATTACAAGAACCCTTTTCCAAAAGAA 478 S I Y L. D H H Y Y K N P E P K E 15 O pLC5. 2 GAAAGGGATCTCTACTCCACATCTCTTGCATTTAGGCTCCTCAGAGAACA 528 E. R. D. L. Y S T S L A E R L. L. R. E. H. 167 pIC5. 2 TGGTTTTCAAGTCGCACAAGAGGTATTCGATAGTTTCAAGAACGAGGAGG 578 G F O V A Q E V F D S F K N E E G 184 pLC5. 2 GTGAGTTCAAAGAAAGCCTTAGCGACGACACCAGAGGATTGTTGCAACTG 628 E F K E S L S D D T R G L L O L 2 OO pIC5. 2 TATGAAGCTTCCTTTCTGTTGACGGAAGGCGAAACCACGCTCGAGTCAGC 678 Y E A S F. L. L T E G E T T L E S A 217 52. 4-cy. U.S. Patent Feb. 16, 1999 Sheet 6 of 9 5,871,988 pIC5. TCGGTGGAAGAGGTGAGCAGAGGGGATGTGCCGAAATCACTTCAGTGCTA 1578 s V E E V S R G D V P K S L Q C Y 517 plC5. CATGAGTGACTACAATGCATCGGAGGCGGAGGCGCGGAAGCACGTGAAAT 1628 M S D Y N A S E A E A R K H. W. K. W. 534 pILC5. GGCTGATAGCGGAGGTGTGGAAGAAGATGAATGCGGAGAGGGTGTCGAAG 1678 L. I. A E W W. K. R. M. N. A E R W S K 550 plC5. GATTCTCCATTCGGCAAAGATTTTATAGGATGTGCAGTTGATTTAGGAAG 1728 D S P F. G. K. D F I G C A W D L G R 567 pILC5. GATGGCGCAGTTGATGTACCATAATGGAGATGGGCACGGCACACA ACACC 1778 M A Q L. M. Y H N G D G H G T Q H P 584 pIC5. CTATTATACATCAACAAATGACCAGAACCTTATTCGAGCCCTTTGCATGA 1828 I I H Q Q M T R T L. F. E. P. F. A 5.99 pIC5. GAGATGATGACGAGCCATCGTTTACTTACTTAAATTCTACCAAAGTTTTT 1878 pIC5. CGAAGGCATAGTTCGTAATTTTTCAAGCACCAATAAATAAGGAGAATCGG 1928 pIC5. CT CAAACAAACGTGGCATTTGCCACCACGTGAGCACAAGGGAGAGTCTGT 1978 plC5. CGTCGTTTATGGATGAACTATTCAATTTTTAIGCATGTAATAATTAAGTT 2028 pIC5. CAAGTTCAAGAGCCTTCTGCATATTTAACTATGTATTTGAATTTATCGAG 2O78 pIC5. TGTGATTTTCTGTCTTTGGCAACATATATTTTTGTCATATGTGGCATCTT 2128 pI C5. ATTATGATATCATACAGTGTTTATGGATGATATGATACTATCAAAAAAAA 21.78 plC5. 2182 52. 22. U.S. Patent Feb. 16, 1999 Sheet 7 of 9 5,871,988 U.S. Patent Feb. 16, 1999 Sheet 8 of 9 5,871,988 Castor Bean 1 MALPSAAMOSNPEKLNLEHRLSSLPTTSLEYGN. NRFPFESSSAKSHFKK 49 . : . : : : : . Spearmint 1. KVLSVATQMAIPSNLTTCLQPSHFKSSPKLLSSTNSSSRS 43 Castor Bean 50 PTQACLSSTTHQEVRPLAYFPPTVWGNRFASLTFNPSEFESYDERVIVLK 99 . : ||. : : - . 1: . Spearmint 44 RLRVYCSSSQLTTERRSGNYNPSRWDVNFIQSLLSDYKEDKETVIRASELV 93 r Castor Bean 100 KKWKDILISSTSDSVETWILIDLLCRLGWSYHFENDIEELLSKIFNSQ.. 147 . : : . : : : : : : : . : . : ... : Spearmint 94 TLVK. MELEKETDQIRQLELIDDLQRMGLSDHFONEFKEILSSIYLDHHY 142 . : : : : : : . : : Toba CCO 1 . MLLATGRKLADTLNLIDIIERLGISYHFEKEIDEIILDQIYNQN. 43 k Castor Bean 148 . PDLVDEKECDLYTAAIVFRVFROHGFKMSSDVFSKFKDSDGKFKESLRG 1.96 ... : . : : : - . | | | | | . : Spearmint 143 YKNPFPKEERDLYSTSLAFRLLREHGFOVAQEVFDSFKNEEGEFKESLSD 1.92 . | | | | | | | . : : - | | | | | . Tobacco 44 . SN. CNDLCTSALOFRLLRQHGENISPEIFSKFQDENGKFKESLAS 87 Castor Bean 197 DAKGMLSLFEASHLSVHGEDILEEAFAFTKDYLQSSAVE. LFPNLKRHI 244 . : : : | | | | . : : . : ... : : Spearmint 193 DTRGLLQLYEASFL.LTEGETTLESAREFATKFLEEKVNEGGVDGDLLTRI 242 . - : ... : : . : . Tobacco 88 DVLGLLNLYEASHVRTHADDILEDALAFSTIHLESAAPH. LKSPLREQV 135 Castor Bean 245 TNALEQPFHSGWPRLEARKEIDLYEADIECRNETLLEFAKLDYNRVQLLH 294 . : : I. : . : I. : : : : . : : . Spearnint 243 AYSLDIPLHWRIKRPNAPVWIEWYRKRPD. MNPVVLELAILDLNIVQAQF 291 . : I : | | | : : : Tobacco 136 THALEQCLHKGV PRVETREFISSIYDKEQSKNNVLL REAKLDFNLLQMLH 1.85 Castor Bean. 295 QQELCQFSKWWKDLNLASDIPYARDRMAEIFFWAVAMYFEPDYAHTRMII 344 : : : : : - : . : : : . : : . : : : Spearmint 292 QEELKESFRWWRNTGFVEKLPFARDRLVECYFWNTGIIEPRQHASARIMM 341 ... : : : : : . : : | | | | | | . : : Tobacco 186 KQELAQVSRWWKDLDFWTTLPYARDRVVECYFWALGVY FEPOYSOARVML 235 Castor Bean 345 AKWWILLISLIDDTIDAYATMEETHILAEAVARWDMSCLEKLPDYMKVIYK 394 : . : . : : . : ... : : : . : : : . : ... : Spearmint 342 GKVNALITVIDDIYDVYGTLEELEQFTDLIRRWDINSIDQLPDYMQLCFL 391 . ET. T. : . : . | | | . : : : Tobacco 236 WKTISMISIVDDTFDAYGTVKELEAYTDAIQRWDINEIDRLPDYMKISYK 285 52. 61. 5,871,988 1 2 DNA ENCODING LIMONENE SYNTHASE cyclization (Croteau and Satterwhite, J.
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