EP1042485A2 - Desaturase - Google Patents

Desaturase

Info

Publication number
EP1042485A2
EP1042485A2 EP98962620A EP98962620A EP1042485A2 EP 1042485 A2 EP1042485 A2 EP 1042485A2 EP 98962620 A EP98962620 A EP 98962620A EP 98962620 A EP98962620 A EP 98962620A EP 1042485 A2 EP1042485 A2 EP 1042485A2
Authority
EP
European Patent Office
Prior art keywords
dna sequence
polypeptide
fatty acid
sequence
organism
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98962620A
Other languages
English (en)
French (fr)
Inventor
Johnathan A. IACR-Long Ashton Res.Station NAPIER
Louise Bristol University MICHAELSON
Keith Bristol University STOBART
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Bristol
Original Assignee
University of Bristol
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GBGB9727256.1A external-priority patent/GB9727256D0/en
Priority claimed from GBGB9814034.6A external-priority patent/GB9814034D0/en
Application filed by University of Bristol filed Critical University of Bristol
Publication of EP1042485A2 publication Critical patent/EP1042485A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
    • C12N9/0083—Miscellaneous (1.14.99)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/82—Vectors or expression systems specially adapted for eukaryotic hosts for plant cells, e.g. plant artificial chromosomes (PACs)
    • C12N15/8241—Phenotypically and genetically modified plants via recombinant DNA technology
    • C12N15/8242—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits
    • C12N15/8243—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine, caffeine
    • C12N15/8247—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine, caffeine involving modified lipid metabolism, e.g. seed oil composition
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K2217/00—Genetically modified animals
    • A01K2217/05—Animals comprising random inserted nucleic acids (transgenic)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Definitions

  • This invention relates to DNA sequences encoding ⁇ 5-fatty acid desaturases, the encoded ⁇ 5-fatty acid desaturases, and applications for the ⁇ 5-fatty acid desaturases.
  • Polyunsaturated fatty acids are important neutraceutically due to their specific health
  • Polyunsaturated fatty acids are the precursors for two major classes of metabolites:
  • prostanoids which include prostaglandins and thromboxanes
  • leukotrienes which include leukotrienes
  • ⁇ 5-fatty acid desaturase catalyses the conversion of dihomogamma linolenic acid (DHL) to
  • Arachidonic acid has a 20 carbon chain with 4 double bonds and is of great importance in
  • Prostaglandins are modulators of hormone action and the potential effects of prostaglandins include the stimulation of inflammation
  • polyunsaturated fatty acids from these sources include solvent extraction, winterization,
  • GLA ⁇ -linolenate
  • DHGLA dihomo- ⁇ (-linolenate
  • AA eicosapentaenoate
  • DHA docosahezaenoate
  • biosynthetic capacity of lower organisms e.g. algae, bacteria, fungi (including
  • Polyunsaturated fatty acid metabolism is of greatest importance in human metabolism.
  • the inventors have surprisingly isolated and characterised a DNA sequence from the
  • the DNA sequences of this invention may enable the cloning
  • Plant and fungal desaturases are mainly integral membrane polypeptides which makes them
  • a first aspect of the invention provides an isolated animal ⁇ 5-fatty acid desaturase and functional portions thereof.
  • a second aspect of the invention provides an isolated C. elegans ⁇ 5-fatty acid desaturase.
  • a third aspect of the invention provides a DNA sequence according to a first or second aspect of the invention comprises at least a portion of the sequence shown in SEQ.2 and equivalents to that sequence, or to portions of that sequence, which encode a functional ⁇ 5-fatty acid desaturase by virtue of the degeneracy of the genetic code.
  • the DNA sequence is derived from a Caenorhabditis elegans DNA sequence.
  • the gene encoding the ⁇ 5-fatty acid desaturase encoded by the cloned gene is 1341 bp long.
  • the protein is 447 amino acids long with an estimated molecular weight of 57 kDa.
  • the DNA sequence encodes a functional ⁇ 5-fatty acid desaturase and comprises at least a portion of the sequence shown in SEQ.l and equivalents to that sequence, or to portions of that sequence, which encode a functional ⁇ 5-fatty acid desaturase by virtue of the degeneracy of the genetic code.
  • the DNA sequence is derived from a Mortierella alpina DNA sequence.
  • the gene encoding the ⁇ 5-fatty acid desaturase encoded by the cloned gene is 1338 bp long.
  • the protein is 446 amino acids long with an estimated molecular weight of 57 kDa.
  • a DNA sequence according to a third aspect of the invention is functional in a mammal.
  • the DNA sequence is expressed in a mammal.
  • the DNA sequence is expressed in a human.
  • the DNA sequence is obtained by modification of a functional natural gene encoding a ⁇ -5 fatty acid desaturase.
  • the modification includes modification by chemical, physical, or biological means without removing a catalytic activity of the enzyme which it encodes.
  • the modification improves a catalytic activity of the enzyme which it encodes.
  • the biological modification includes recombinant DNA methods and forced evolution techniques.
  • the forced evolution technique is DNA shuffling.
  • a fourth aspect of the invention provides a polypeptide encoded by a DNA sequence according to a third aspect of the invention.
  • polypeptide has the sequence shown in SEQ.3 or functional equivalents to that sequence or portions of that sequence.
  • polypeptide has the sequence shown in SEQ.4 or functional equivalents to that sequence or portions of that sequence.
  • the polypeptide catalyses the conversion of dihomogamma linolenic acid to arachidonic acid.
  • the polypeptide has been modified without removing the catalytic activity of the encoded polypeptide.
  • the polypeptide has been modified in such a way as to introduce a specific level of saturation of a substrate at a specific location within the molecular structure of the substrate.
  • a fifth aspect of the invention provides a vector containing a DNA sequence of any portion of a DNA sequence according to a third aspect of the invention..
  • a sixth aspect of the invention provides a method of producing polyunsaturated fatty acids comprising contacting a substrate with a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention, or a polypeptide according to a fourth aspect of the invention.
  • a seventh aspect of the invention provides a method of converting dihomogamma linoleic acid to arachidonic acid wherein the conversion is catalysed by a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention, or a polypeptide according to a fourth aspect of the invention.
  • An eighth aspect of the invention provides an organism engineered to produce high levels of a polypeptide according to a fourth aspect of the invention.
  • a ninth aspect of the invention provides an organism engineered to produce high levels of a product of a reaction catalysed by a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention, or by a polypeptide according to a fourth aspect of the invention.
  • the organism has been engineered to carry out the method according to a sixth or seventh aspect of the invention.
  • the organism is a microorganism.
  • the microorganism is selected from algae, bacteria and fungi.
  • the fungi includes phycomycetes.
  • the microorganism is a yeast.
  • the organism is a plant.
  • the plant is selected from oil seed plants.
  • the oil seed plants are selected from oil seed rape, sunflower, cereals including maize, tobacco, legumes including peanut and soybean, safflower, oil palm, coconut and other palms, cotton, sesame, mustard, linseed, castor, borage and evening primrose.
  • a tenth aspect of the invention provides a seed or other reproductive material derived from an organism according to a ninth aspect of the invention.
  • the organism is a mammal.
  • An eleventh aspect of the invention provides an isolated multienzyme pathway wherein the pathway includes a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention.
  • a twelfth aspect of the invention provides a compound produced by a conversion of a substrate, wherein said conversion is catalysed by a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention.
  • a thirteenth aspect of the invention provides an intermediate compound produced by the reaction catalysed by a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention.
  • a fourteenth aspect of the invention provides a foodstuff or dietary supplement containing a polyunsaturated fatty acid produced by a method according to a sixth aspect of the invention.
  • a fifteenth aspect of the invention provides a pharmaceutical preparation containing a polyunsaturated fatty acid produced by a method according to a sixth aspect of the invention.
  • a sixteenth aspect of the invention provides prostaglandins synthesised by a biosynthetic pathway including a catalytic activity of a ⁇ 5-fatty acid desaturase according to a first or second aspect of the invention.
  • a seventeenth aspect of the invention provides a method for the modulation of prostaglandins synthesis by the control of the levels of expression of a DNA sequence according to a third aspect of the invention.
  • An eighteenth aspect of the invention provides a probe comprising all or part of a DNA sequence according to a third aspect of the invention,or an equivalent RNA sequence.
  • a nineteenth aspect of the invention provides a probe comprising all or part of a ⁇ 5-fatty acid desaturase polypeptide according to a fourth aspect of the invention.
  • a twentieth aspect of the invention provides a method of isolating ⁇ 5-fatty acid desaturases using a probe according to a nineteenth aspect of the invention.
  • gene of the invention may be transformed into human cells and
  • SEQ.l is a cDNA sequence encoding ⁇ 5-fatty acid desaturase from Mortierella alpina and;
  • SEQ.2 is a cDNA sequence encoding ⁇ 5-fatty acid desaturase from C. elegans.
  • SEQ.3 is the peptide sequence obtained by translating the gene sequence of SEQ.l.
  • SEQ.4 is the peptide sequence obtained by translating the gene sequence of SEQ2;
  • Fig.1 is a line-up of the gene encoding Mortierella alpina ⁇ 5-fatty acid desaturase with
  • Fig. 2 is a line-up of the gene encoding ⁇ 5-fatty acid desaturase with the C. elegans ⁇ 6
  • Fig. 3 is a gas chromatography trace of the fatty acid methyl esters of induced yeast cell
  • Fig. 4 is a gas chromatography trace of the fatty acid methyl esters of induced yeast cell
  • DNA sequences of the invention encode ⁇ 5-fatty acid desaturases and were cloned
  • DHL dihanogamma linolenic acid
  • AA arachidonic acid
  • ETA eicostatetraenoate
  • PCR Chain Reaction
  • DP degenerate oligonucleotide primers
  • amplification products were separated on 1 % agarose gels.
  • primers (P) based on the 660 bp product sequence.
  • Mortierella alpina cDNA library The fragment probe hybridised to 25 out of the 3.5 x 10 5 phage clones screened and one clone was shown, by restriction analysis, to have the
  • LI 1 This clone, designated LI 1, was selected for further analysis. Sequence analysis of LI 1 revealed an open reading frame of 1 ,338 bp in length encoding a
  • polypeptide of 446 amino acids When analyzed on the protein and genomic databases
  • LI 1 showed a low level 20% identity to the ⁇ 6 desaturase gene from Synechocystis sp.
  • sequence contains the variant QXXHH.
  • the translated sequence also contains a
  • cytochrome bs-like heme-binding domain at the N-terminus which includes the EHPGG
  • the 660 bp PCR product was gel purified and Southern blots of restricted Mortierella
  • cDNA was subcloned into the yeast expression vector, pYES2, supplied by Invitrogen TM
  • the estimated molecular weight of the product was 55-60
  • transgenic yeast were capable of desaturating Dihomo gamma linolenic acid at the ⁇ 5
  • MS80RFA operating at an ionization voltage of 70 eV with a scan range of 500-40 daltons
  • Mortierella alpina encodes a functional polypeptide involved in the synthesis of arachidonic acid in the presence of galactose and dihomo gamma linolenate.
  • cosmid T13F2 contained an open reading frame (ORF),
  • T13F2.1 which contained an N-terminal cytochrome b 5 domain (defined by the
  • microsomal desaturases contained a variant third histidine
  • glutamate substitution is present in both plant and animal ⁇ 6-fatty acid desaturases and in
  • PCR polymerase chain reaction
  • a DNA fragment of the correct predicted size was amplified (as visualised on a 1 %
  • Plasmid L4 was released from ⁇ clone L4 by excision and the cDNA
  • YCEDFor 5'-GCGAAGCTTAAAATGGTATTACGAGAGCAAGAGC-3' (annealing to the initiating methionine is indicated by the bold type face and the Hind HI
  • the amplified PCR product containing the complete coding region of L4 was ligated into
  • yeast expression vector pYES2 (Invitrogen), downstream of the GAEl promoter using
  • the translation product obtained from pYES2/L4 had a molecular weight of approximately
  • the fatty acid produced from di-homo- ⁇ -linolenic acid was further characterised by GCMS (Gas Chromatography Mass Spectrometry) and identified as arachidonic acid.
  • GCMS Gas Chromatography Mass Spectrometry

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Plant Pathology (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Cell Biology (AREA)
  • Nutrition Science (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
  • General Preparation And Processing Of Foods (AREA)
EP98962620A 1997-12-23 1998-12-23 Desaturase Withdrawn EP1042485A2 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB9727256 1997-12-23
GBGB9727256.1A GB9727256D0 (en) 1997-12-23 1997-12-23 Desaturase gene
GBGB9814034.6A GB9814034D0 (en) 1998-06-29 1998-06-29 Desaturase gene
GB9814034 1998-06-29
PCT/GB1998/003895 WO1999033958A2 (en) 1997-12-23 1998-12-23 Desaturase

Publications (1)

Publication Number Publication Date
EP1042485A2 true EP1042485A2 (de) 2000-10-11

Family

ID=26312844

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98962620A Withdrawn EP1042485A2 (de) 1997-12-23 1998-12-23 Desaturase

Country Status (11)

Country Link
EP (1) EP1042485A2 (de)
JP (1) JP2002508932A (de)
KR (1) KR20010033517A (de)
CN (1) CN1283230A (de)
AU (1) AU1774899A (de)
BR (1) BR9814434A (de)
CA (1) CA2315297A1 (de)
EE (1) EE200000372A (de)
HU (1) HUP0101153A3 (de)
PL (1) PL344868A1 (de)
WO (1) WO1999033958A2 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8791327B2 (en) 1998-12-07 2014-07-29 Washington State University Research Foundation Desaturases and methods of using them for synthesis of polyunsaturated fatty acids
AU2001263473A1 (en) * 2000-05-26 2001-12-11 Washington State University Research Foundation Palmitate desaturase gene
DE60141760D1 (de) 2000-09-28 2010-05-20 Bioriginal Food & Science Corp Fad4, fad5, fad5-2, and fad6, mitglieder der fettsäuredesaturasefamilie und ihre verwendungen
GB0107510D0 (en) 2001-03-26 2001-05-16 Univ Bristol New elongase gene and a process for the production of -9-polyunsaturated fatty acids
GB0229578D0 (en) * 2002-12-19 2003-01-22 Univ Bristol Novel method for the production of polyunsaturated fatty acids
GB0403452D0 (en) * 2004-02-17 2004-03-24 Univ York Desaturase enzymes
CA3023314C (en) 2004-04-22 2019-12-10 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
DK1756280T3 (en) 2004-04-22 2015-02-02 Commw Scient Ind Res Org SYNTHESIS OF CHAIN, polyunsaturated fatty acids BY RECOMBINANT CELLS
ES2351973T3 (es) 2004-06-04 2011-02-14 Fluxome Sciences A/S Células metabólicamente modificadas por ingeniería para la producción de ácidos grasos poliinsaturados.
JP4691032B2 (ja) 2004-07-12 2011-06-01 サントリーホールディングス株式会社 Δ５脂肪酸不飽和化活性を有するポリペプチドおよびそのポリペプチドをコードするポリヌクレオチドならびにそれらの利用
GB2431158A (en) 2005-10-13 2007-04-18 Rothamsted Res Ltd Process for the production of arachidonic and/or eicosapentaenoic acid
AU2007291937B2 (en) 2006-08-29 2014-05-15 Commonwealth Scientific And Industrial Research Organisation Synthesis of fatty acids
CN101376020B (zh) * 2007-08-29 2013-05-01 益生生技开发股份有限公司 真菌免疫调节蛋白在抑制△5-去饱和酶中的应用
CA3015426C (en) 2008-11-18 2020-01-14 Commonwealth Scientific And Industrial Research Organisation Recombinant cells comprising exogenous .delta.5 and .delta.6 desaturases, .delta.5 and .delta.6 elongases, and .delta.4 desaturases
NZ631702A (en) 2012-06-15 2017-01-27 Grains Res & Dev Corp Production of long chain polyunsaturated fatty acids in plant cells
EP3082405A4 (de) 2013-12-18 2017-12-13 Commonwealth Scientific and Industrial Research Organisation Lipid mit langkettigen mehrfach ungesättigten fettsäuren
PH12016502586B1 (en) 2014-06-27 2023-07-19 Commw Scient Ind Res Org Lipid comprising docosapentaenoic acid

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5972664A (en) * 1997-04-11 1999-10-26 Abbott Laboratories Methods and compositions for synthesis of long chain poly-unsaturated fatty acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SATOUCHI K ET AL: "Phospholipids from free-living nematode Caenorhabditis elegans", LIPIDS, vol. 28, no. 9, September 1993 (1993-09-01), pages 837 - 840 *

Also Published As

Publication number Publication date
HUP0101153A3 (en) 2006-03-28
CN1283230A (zh) 2001-02-07
CA2315297A1 (en) 1999-07-08
WO1999033958A2 (en) 1999-07-08
JP2002508932A (ja) 2002-03-26
PL344868A1 (en) 2001-11-19
BR9814434A (pt) 2001-10-23
HUP0101153A2 (hu) 2001-08-28
WO1999033958A3 (en) 1999-09-02
EE200000372A (et) 2001-12-17
KR20010033517A (ko) 2001-04-25
AU1774899A (en) 1999-07-19

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