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W O 2016/075310 A1 W Ipo I (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date W O 2016/075310 A1 19 May 2016 (19.05.2016) W IPO I PCT (51) International Patent Classification: lin (DE). ANDRE, Carl; 1012 Winona Road, Raleigh, C12N15/82 (2006.01) North Carolina 27609 (US). (21) International Application Number: (74) Agent: POPP, Andreas; Global Intellectual Property, PCT/EP2015/076605 ZRX/B, 67056 Ludwigshafen (DE). (22) International Filing Date: (81) Designated States (unless otherwise indicated,for every 13 November 2015 (13.11.2015) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (25) Filing Language: English BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (26) Publication Language: English DO, DZ, EC, EE, EG, ES, Fl, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (30) Priority Data: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, 62/079,622 14 November 2014 (14.11.2014) US MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 62/234,373 29 September 2015 (29.09.2015) US PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (71) Applicant: BASF PLANT SCIENCE COMPANY SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, GMBH [DE/DE]; Carl-Bosch-Str. 38, 67056 Ludwig- TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. shafen am Rhein (DE). (84) Designated States (unless otherwise indicated,for every (72) Inventors: SENGER, Toralf; 609 Cheselden Drive, kind of regional protection available): ARIPO (BW, GH, Durham, 27713 (US). MARTY, Laurent; Neue Stuecker GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 21, 69118 Heidelberg (DE). KUNZE, Irene; Muehlenweg TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 11, 06466 Gatersleben (DE). HAERTEL, Heiko; Rudolf- TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, Reusch-Str. 23D, 10367 Berlin (DE). BREMMER, DK, EE, ES, Fl, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Steven; 1604 Kelvington Place, Apex, 27502 (US). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, BREAZEALE, Steven; 462 Neodak Rd., Apex, 27523 SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (US). BAUER, Joerg; 1004 Scholastic Circle, Durham, GW, KM, ML, MR, NE, SN, TD, TG). North Carolina 27713 (US). VRINTEN, Patricia; 725 310 Published: Stillwater Drive, Saskatoon, S7J 4H5 (CA). STYMNE, -a Sten; Radmansgatan 1, 26132 Landskrona (SE). LIND- with internationalsearch report (Art. 21(3)) BERG YILMAZ, Jenny; Per Ols vdg 9, 23737 Bfdrred with sequence listing part of description (Rule 5.2(a)) (SE). MCELVER, John; 722 Blackard Rd., Roxboro, 27574 (US). REIN, Dietrich; Flottwellstr. 3A, 10785 Ber (54) Title: STABILISING FATTY ACID COMPOSITIONS Fig. 1 -6- aerobic 03 - pathway 1 233 pathway -199ba e ngase 2 6-desatwa4e2 9eorgase Ac2et2y"- 1 18.4 W-desaturs e 1 gdesaturase 0205 2024 5desaturase- PKS (anaerobic) Sprecher pathway 0 desarorase A6-desat irase 22:6 " 22 p-oxidation (57) Abstract: Assay method, comprising providing a plant capable of expressing a delta- 12 desaturase, wherein said delta- 12 desat urase has at least 50% total amino acid sequence identity to at least one of the sequences SEQ ID NO. 328 to 336, and/or at least N 59% total amino acid sequence similarity to at least one of the sequences SEQ ID NO. 328 to 336,and wherein the plant is also cap able of expressing at least one or more enzymes of unsaturated fatty acid metabolism, of which enzymes at least one is capable of us ing linoleic acid as a substrate, and of which enzymes at least one is supposedly connected to a plant metabolic propertygrowing the plant, and measuring said plant metabolic property for said plant. WO 2016/075310 PCT/EP2015/076605 Stabilising fatty acid compositions FIELD OF THE INVENTION 5 This application claims priority to U.S. Provisional Patent Application Serial Number 62/079622 application number filed November 14, 2014 and to U.S. Provisional Patent Application Serial Number 62/234373 filed September 29, 2015, which are incorporated herein by reference in their entirety. 10 The Sequence Listing, which is a part of the present disclosure, is submitted concurrently with the specification as a text file. The subject matter of the Sequence Listing is incorporated herein in its entirety by reference. The present invention is concerned with materials and methods for the production of genetically 15 modified plants, particularly where the plants are for the production of at least one unsaturated or polyunsaturated fatty acid. The invention is also concerned with identification of genes conveying an unsaturated fatty acid metabolic property to a plant or plant cell, and generally relates to the field of Delta-12 desaturases. 20 BACKGROUND OF THE INVENTION For the production of genetically modified plants it is not sufficient to test the effects of nucleic acid sequences in plants under greenhouse conditions. Unfortunately it has frequently been observed that plant metabolic properties differ in unpredictable ways when plants are grown in 25 our field or under greenhouse conditions. Thus, when developing genetically modified plants having altered metabolic properties compared to the corresponding wild-type plant, it is necessary to test such plants in field trials. However, field trials entail a variety of disadvantages compared to plant growth under greenhouse 30 conditions: for example, field trial plots have frequently been vandalised or devastated by animals, rendering all work of creating the originally planted plants and sending them on the field useless. Further, field trials require completion of Norma Rose procedures of regulatory supervision, making field trials rather cumbersome. Also, the amount of practical work in raising enough plants for a future test, devising a plot layout to plant the plants, and planting and monitoring the plants 35 is more labour intensive than testing plants under greenhouse conditions, particularly as plant maintenance and monitoring work can be highly automated in the greenhouse. Furthermore, growing plants in an automatic greenhouse allows to inspect plant parts that are not readily accessible on a field, for example because on a field the plants are grown too densely or the interesting plant part is growing underground, for example plant roots. Thus it is generally desired 40 to reduce the number of necessary field trials. This is particularly true in the field of production of polyunsaturated fatty acids. Plants generally cannot produce unsaturated fatty acids of at least 20 carbon atoms in length and comprising at WO 2016/075310 PCT/EP2015/076605 least two double bonds. Thus, to develop plants for the production of such unsaturated fatty acids, it is necessary to install the whole metabolic process starting from linoleic acid or iPhone-linolenic acid. Even though potentially suitable elongates and desaturase genes are known in the art and have been tested at least in model plants, it is uncertain which combinations of genes and 5 promoters will provide economically satisfactory yields of unsaturated fatty acids in a stable way, particularly under the environmental conditions that change from growth period to growth period. Thus, field trials cannot be avoided when developing plants for the production of unsaturated fatty acids. One of the factors that has to be a certain and by field trials is whether or not the composition of the plant oil will be as expected even under field conditions. It has unfortunately 10 been observed that the composition of plant oils measured in individual plant seeds greatly differs even for seeds obtained from the very same plant, and particularly varies between plants grown under differing conditions. Thus, the composition of a plant oil obtained from harvesting a plurality of plants grown under field conditions cannot always reliably been predicted on the basis of oil composition analyses of individual plant seeds taken from plants grown under greenhouse 15 conditions. Reproducible production of a specific fatty acid profile is particularly important for commercial canola oil production. There is need to identify ways to reduce the variability in the fatty acid profile of canola oils produced in different environments. 20 The invention thus and generally aspires to remove or alleviate the above identified shortcomings and to provide materials and methods useful for reducing the number of field trials required for the manufacturing of a marketable plant variety producing unsaturated fatty acids. Further aspects and embodiments of the invention will become apparent below. 25 BRIEF DESCRIPTION OF THE FIGURES Figure 1: Schematical figure of the different enzymatic activities leading to the production of ARA, EPA and DHA 30 Figure 2: Formulas to calculate pathway step conversion efficiencies. S: substrate of pathway step. P: product of pathway step. Product was always the sum of the immediate product of the conversion at this pathway step, and all downstream products that passed this pathway step in order to be formed. E.g. DHA (22:6n-3 does possess a double bond that was a result of the delta 35 12-desaturation of oleic acid (18:1n-9) to linoleic acid (18:2n-6). Figure 3: Strategy employed for stepwise buildup of plant expression plasmids of the invention. Figure 4: Stabiliy of binary plant expression plasmids containing the CoIE1/pVS1 origin of 40 replication for plasmid recplication in E.coli/Agrobacteria. Left Panel: Stability in Agrobacterium cells by isolating plasmid DNA from Agrobacterium cutures prior to usage of this culture for plant transformation, and subjecting the plasmid DNA to a restriction digest.
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