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(12) United States Patent (10) Patent No.: US 6,706,501 B1 Ross0n Et Al USOO6706501B1 (12) United States Patent (10) Patent No.: US 6,706,501 B1 ROSS0n et al. (45) Date of Patent: Mar. 16, 2004 (54) POLYNUCLEOTIDE ENCODING A Hamberg, Biochem. and BiophyS. Res. Comm., 188(3): PROPIONIBACTERIUM LINOLEATE 1220–1227 (1992). SOMERASE AND USES THEREOF Hart et al., J. Virol.., 70.3606–3616 (1996) Sequence Search. Hughes et al., J. Biological Chemistry, 257(7):3643-3649 (75) Inventors: Reinhardt A. Rosson, Manitowoc, WI (1982). (US); Ming-De Deng, Manitowoc, WI Hunter et al., J. Biological Chemistry, 251 (8):2241-2247 (US); Alan D. Grund, Manitowoc, WI (1976). (US) Jack et al., Clinica Chimica Acta, 224:139-146 (1994). Jiang et al., J. Applied Microbiology, 85:95-102 (1998). (73) Assignee: Arkion Life Sciences LLC, Kemp et al., J. General Microbiology, 130:527–533 (1984). Wilmington, DE (US) Kemp et al., British J. Nutrition, 52:165–170 (1984). (*) Notice: Subject to any disclaimer, the term of this Kemp et al., British J. Nutrition, 52:171-177 (1984). patent is extended or adjusted under 35 Kemp et al., J. General Microbiology, 90:100-114 (1975). U.S.C. 154(b) by 0 days. Kepler et al., J. Biological Chemistry, 242(24):5686-5692 (1967). Kepler et al., Methods in Enzymology, 14:105-110 (1969). (21) Appl. No.: 09/561,077 Kepler et al., J. Biological Chemistry, 241(6):1350-1354 (22) Filed: Apr. 28, 2000 (1966). Kepler et al., J. Biological Chemistry, 245(14):3612-3620 Related U.S. Application Data (1970). (60) Provisional application No. 60/141,798, filed on Jun. 30, Kepler et al., J. Biological Chemistry, 246(9):2765-2771 1999. (1971). Kil et al., Infect. Immun., 62:2440-2449 (sequence search) (51) Int. Cl. ........................... C12P 7/64; CO7H 21/04; (1994). C12N 1/20 Klein et al., 1983, Immobilized Microbial Cells, vol. 4, pp. 11-51, "Methods for the Immobilization of Microbial (52) U.S. Cl. .................... 435/134; 435/233; 435/235.1; Cells”, In Wingard & Katchalski-Katzir (eds.) Academic 435/325; 435/348; 435/419, 435/252.3; Press. 435/254.11; 435/254.2; 435/252.31; 435/252.33; Koritala et al., Applied Microbiology and Biotechnology, 435/257.2; 435/174; 435/320.1; 536/232; 32:299-304 (1989). 536/23.7; 536/24.3 Lanser, J. American Oil Chemists Society, 75(12):1809–1813 (1998). (58) Field of Search ................................. 435/174, 233, Lilly, Chemical Engineering Science, 49(2):151-159 435/252.3, 254.11, 257.2, 348, 325, 419, (1994). 252.31, 252.33, 254.2, 320.1, 235.1, 134; Mills et al., Australian J. of Biological Sciences, 536/23.2, 23.7, 24.3 23:1109-1113 (1970). (56) References Cited Mortimer et al., J. Biological Chemistry, 249(9):2833–2842 (1974). U.S. PATENT DOCUMENTS Niehaus, Mechanisms of cis-trans isomerization of unsat 5,856,149 A 1/1999 Pariza et al. ................ 435/134 urated fatty acids, pp. 229-245, In E.E. van Tamelen (ed.) 6,015,833. A 1/2000 Saebos et al. ................. 514/558 Bioorganic Chemistry, Academic Press, New York, 1977. Niehaus et al., J. Bacteriology, 134(1):177-183 (1978). FOREIGN PATENT DOCUMENTS Niehaus et al., J. Biological Chemistry, 245(15):3790-3797 WO WO 96/38137 12/1996 (1970). WO WO 99/29886 6/1999 (List continued on next page.) OTHER PUBLICATIONS Primary Examiner Rebecca E. Prouty Burgess et al., Lipids, 26(2):162-165 (1991). ASSistant Examiner David J Steadman Chibata, 1978, Immobilized Enzymes, pp. 73–81, Halsted (74) Attorney, Agent, or Firm-Sheridan Ross P.C. PreSS, Japan. Eyssen et al., Amer. J. Clin. Nutrition, 27:1329-1340 (1974). (57) ABSTRACT Eyssen et al., Applied and Environmental Microbiol., The present invention provides an isolated (trans,cis)-10,12 47(1):39–43 (1984). linoleate isomerase and its nucleic acid and amino acid Faber, Ch 3. Special Techniques, pp. 270–340. In (ed.), Sequences. The present invention also provides a method for Biotransformations in organic chemistry (1995). producing conjugated linoleic acid or conjugated linolenic Fujimoto et al., BioScience and Biotechnology Biochemistry, acid (CLA), or derivatives thereof, from an oil using an 57(6):1026–1027 (1993). immobilized cell and/or an isolated linoleate isomerase. The Fukui et al., Endeavour, New Series, 9(1):10–17 (1985). present invention also provides an isolated lipase-like pro Garcia et al., Biochimica et Biophysica Acta, 424:296-302 tein and its nucleic acid and amino acid Sequences. The (1976). present invention also provides an isolated Giesel-Bihler et al., 1986, The anearobic transformation of acetyltransferase-like enzyme and its nucleic acid and amino linoleic acid by Acetobacterium woodii. International Sym acid Sequences. posium-Biocatalysis in organic media. Wageningen, The Netherlands. Elsevier Science Publishers B.V. 51 Claims, 59 Drawing Sheets US 6,706,501 B1 Page 2 OTHER PUBLICATIONS Uchida et al., General and Applied Microbiology, Niehaus et al., J. Biological Chemistry, 245(15):3802–3809 18:109–129 (1972). (1970). Uchida et al., J. General and Applied Microbiology, Park et al., J. Food Sci. and Nutr., 1(2):244-251 (1996). 19:233-249 (1973). Polan et al., J. Bacteriology, 88(4): 1056–1064 (1964). Van Sonsbeek et al., Enzyme and Microbial Technology, Powell, 1996, Chapter 2.14 -Immobilized Enzymes, pp. 15:722-729 (1993). 267–272, In T. Godfrey and S. West (ed.), Industrial Enzy Verhulst et al., Systematic and Applied Microbiology, mology. The Nature Press, New York. 9:12–15 (1987). Sako et al., Nucleic Acids Res., 11:7679-7693 (sequence Verhulst et al., Appl. Environ Microbiol., 51(3):532–538 search) (1983). (1986). Schwab et al., Chemical Reviews, 90:1203–1245 (1990). Seltzer, 1972, Cis-Trans Isomerization, pp. 381–406, In P.D. Verhulst et al., FEMS Microbiology Ecology, 31:255-259 Boyer (ed.), The Enzymes, Academic Press, New York. (1985). Seo et al., Agricultural Biological Chemistry, Wise et al., Biochemistry, 36(10):2985-2992 (1998). 45(9):2025-2030 (1981). Wise et al., Experientia, 52:88-92 (1996). Swaisgood, (1985), Chapter 1-Enzymes and Immobilized Yamazaki et al., J. Biological Chemistry, cells in Biotechnology, pp. 1-24, In Allen I. Laskin (ed.), 254(10):3812–3817 (1979). New Jersey Center for Advanced Biotechnology and Medi cine, New Jersey. Miskin et al., Microbiology, 143:1745–1755 (1997). Tulloch, Lipids, 17:544–550 (1982). Steiner et al., Can. J. Microbiol., 43:315-321 (1997). Uchida, Biochimica et Biophysica Acta, 348:86-93 (1974). Yang, “Isolation, identification and characterization of Uchida, Agricultural and Biological Chemistry, linoleate isomerase from Lactobacillus reuteri” (1997) 180 39(2):561-563 (1975). pp., UMI Order No. DA9823268. U.S. Patent US 6,706,501 B1 G U.S. Patent Mar. 16, 2004 Sheet 4 of 59 US 6,706,501 B1 --25562 (aerobfc) LA -o-25562 (aerobic) CLA HOURS FG. 4 U.S. Patent Mar. 16, 2004 Sheet S of 59 US 6,706,501 B1 25OO - HLNOLECACD -C- CLA 2OOO 1500 1 OOO 500 HOURS F.G. 5 U.S. Patent US 6,706,501 B1 U.S. Patent Mar. 16, 2004 Sheet 8 of 59 US 6,706,501 B1 ?HTHEC×CK×O-C××××××××××××××××××××××××00’0 U.S. Patent Mar. 16, 2004 Sheet 9 of 59 US 6,706,501 B1 -o- C D ISOM E FG. 9 U.S. Patent Mar. 16, 2004 Sheet 10 of 59 US 6,706,501 B1 A - T A - T A - T G - C T G C - G G - C A - T A - T G - C A - T A - T 5-TTA CTA TAA AGA TGA - TTTTTATA-3' L L STOP FIG 10 U.S. Patent Mar. 16, 2004 Sheet 11 of 59 US 6,706,501 B1 Tested TWO Constructs Fac isom ATG #1 ORF T 2 2. ma-musemale to- Ho ATG ii.2 ORF -alo re New Construct #3: ORF HisTag New Construct #4: Partial ORF HisTag O/N/N/N/ FIG 11 U.S. Patent Mar. 16, 2004 Sheet 12 of 59 US 6,706,501 B1 Expression System: Hapll promoter LAT promoter - with the Secretion signal peptide - without the Secretion signal peptide hapl ORF #1 Flat S.O. ORF 2 ORF HisTag it:3 Partial ORF if4 ORF #5 Partial ORF #6 FG12 U.S. Patent Mar. 16, 2004 Sheet 13 of 59 US 6,706,501 B1 Total Cell Lysate: Cells lysed with lysozyme and broken by Sonication Centrifugation: 10,000 g, 30 min - T - Supernatant Pelet (Crude Extract) (Inclusion Body) Centrifugation: Lysis buffer, Tween 20, 45 k rpm, 90 min EGTA, Shaken 1 h Centrifugation: 10,000 g, 30 min Supernatant Membrane (Soluble Protein) Pellet Supernatant-1 || Pellet-1 Lysis buffer, Lysis buffer, Tween 20, Tween 20, EGTA, Shaken EGTA, Shaken overnight overnight Centrifugation: Centrifugation: 45 k rpm, 90 min 10,000 g, 30 min Supernatant (Solubilized Unsolubilized Supernatant-2 Pelet-2 Membrane Membrane Pellet Proteins) F.G. 13 U.S. Patent Mar. 16, 2004 Sheet 14 of 59 US 6,706,501 B1 500 - HLNOLEIC ACD -o-10,12-CLA 400 - 3OO . D Ol ?h 200 - 1 OO O C. | : E O 5 10 15 20 25 30 35 40 45 50 55 60 65 70 HOURS F.G. 14 U.S. Patent Mar. 16, 2004 Sheet 15 of 59 US 6,706,501 B1 P. acnes Culture Harvest, Wash, Suspend in Buffer French PreSS 15K/30 minutes Crude Extract (A) Particulate -- 45K/90 minutes - -> Soluble (B) Fraction Fraction Buffer Wash 45K/90 minutes - - - Washed (C) N Pellet 45K Wash (D) FG.15 U.S. Patent Mar. 16, 2004 Sheet 16 of 59 US 6,706,501 B1 1 OO - 80 - 6 O 4 O 2O - U.S.
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