The front-end desaturase: Structure, function, evolution and biotechnological use

Lipids

Volumn 47, Issue 3, 2012, Pages 227-237

  Meesapyodsuk, Dauenpen ^a,b   Qiu, Xiao ^a,b  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Biotechnology; Desaturases; General area; Lipid biochemistry; N 3 fatty acids; N 6 fatty acids; Polyunsaturated fatty acids (PUFA)

Indexed keywords

ACYL COENZYME A DESATURASE 1; ARACHIDONIC ACID; CYTOCHROME B5; DOCOSAHEXAENOIC ACID; DOCOSAPENTAENOIC ACID; ICOSAPENTAENOIC ACID; LINOLEOYL COENZYME A DESATURASE; OXYGENASE; ACYL COENZYME A DESATURASE;

AMINO TERMINAL SEQUENCE; BINDING AFFINITY; BIOCATALYSIS; BIOTECHNOLOGICAL PROCEDURES; BIOTECHNOLOGICAL PRODUCTION; DELTA 4 DESATURASE GENE; DELTA 5 DESATURASE GENE; DELTA 6 DESATURASE GENE; DELTA 8 DESATURASE GENE; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; FATTY ACID DESATURATION; FATTY ACID SYNTHESIS; FUNCTIONAL MORPHOLOGY; GENE; HUMAN; MOLECULAR CLONING; MOLECULAR EVOLUTION; MOLECULAR INTERACTION; NONHUMAN; ORGANISMS BY ELECTRON DONOR; PROTEIN DOMAIN; PROTEIN FUNCTION; REVIEW; STRUCTURE ANALYSIS; ANIMAL; CATALYSIS; CHEMISTRY; METABOLISM; PHYLOGENY; STRUCTURE ACTIVITY RELATION;

ALGAE; ANIMALIA; ARA; CYANOBACTERIA; EUKARYOTA; FUNGI; PROTOZOA;

ANIMALS; CATALYSIS; DOCOSAHEXAENOIC ACIDS; EVOLUTION, MOLECULAR; FATTY ACID DESATURASES; HUMANS; PHYLOGENY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862268506     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-011-3617-2     Document Type: Review

References (102)

1. Shanklin J, Cahoon EB (1998) Desaturation and related modifications of fatty acids. Annu Rev Plant Physiol Plant Mol Biol 49:611-641
2. Los DA, Murata N (1998) Structure and expression of fatty acid desaturases. Biochim Biophys Acta 1394:3-15 (Pubitemid 28451571)
3. Buist PH (2004) Fatty acid desaturases: selecting the dehydrogenation channel. Nat Prod Rep 21:249-262 (Pubitemid 38527318)
4. Yadav NS, Wierzbicki A, Aegerter M, Caster CS, Perez-Grau L, Kinney AJ, Hitz WD, Booth JR Jr, Schweiger B, Stecca KL (1993) Cloning of higher plant omega-3 fatty acid desaturases. Plant Physiol 103:467-476 (Pubitemid 2005292)
5. Hitz WD, Carlson TJ, Booth JR Jr, Kinney AJ, Stecca KL, Yadav NS (1994) Cloning of a higher-plant plastid omega-6 fatty acid desaturase cDNA and its expression in a cyanobacterium. Plant Physiol 105:635-641
6. Reed DW, Schafer UA, Covello PS (2000) Characterization of the Brassica napus extraplastidial linoleate desaturase by expression in Saccharomyces cerevisiae. Plant Physiol 122:715-720
7. Meesapyodsuk D, Reed DW, Covello PS, Qiu X (2007) Primary structure, regioselectivity, and evolution of the membranebound fatty acid desaturases of Claviceps purpurea. J Biol Chem 282:20191-20199 (Pubitemid 47100013)
8. Fox BG, Shanklin J, Somerville C, Munck E (1993) Stearoylacyl carrier protein delta 9 desaturase from Ricinus communis is a diiron-oxo protein. Proc Natl Acad Sci USA 90:2486-2490 (Pubitemid 23078652)
9. Fox BG, Shanklin J, Ai J, Loehr TM, Sanders-Loehr J (1994) Resonance Raman evidence for an Fe-O-Fe center in stearoyl-ACP desaturase. Primary sequence identity with other diironoxo proteins. Biochemistry 33:12776-12786
10. Spychalla JP, Kinney AJ, Browse J (1997) Identification of an animal omega-3 fatty acid desaturase by heterologous expression in Arabidopsis. Proc Natl Acad Sci USA 94:1142-1147
11. Meesapyodsuk D, Reed DW, Savile CK, Buist PH, Ambrose SJ, Covello PS (2000) Characterization of the regiochemistry and cryptoregiochemistry of a Caenorhabditis elegans fatty acid desaturase (FAT-1) expressed in Saccharomyces cerevisiae. Biochemistry 39:11948-11954
12. Qiu X, Hong H, MacKenzie SL (2001) Identification of a Delta 4 fatty acid desaturase from Thraustochytrium sp. involved in the biosynthesis of docosahexanoic acid by heterologous expression in Saccharomyces cerevisiae and Brassica juncea. J Biol Chem 276:31561-31566
13. Aitzetmuller K, Tsevegsuren N (1994) Seed fatty acid "frontend" desaturases and chemotaxonomy-a case study in the Ranunculaceae. J Plant Physiol 143:538-543
14. Nakamura MT, Nara TY (2004) Structure, function, and dietary regulation of delta6, delta5, and delta9 desaturases. Annu Rev Nutr 24:345-376
15. 5 domain results in the accumulation of high levels of delta6-desaturated fatty acids in transgenic tobacco. Proc Natl Acad Sci USA 94:4211-4216
16. Garcia-Maroto F, Garrido-Cardenas JA, Rodriguez-Ruiz J, Vilches-Ferron M, Adam AC, Polaina J, Alonso DL (2002) Cloning and molecular characterization of the delta6-desaturase from two echium plant species: production of GLA by heterologous expression in yeast and tobacco. Lipids 37:417-426 (Pubitemid 34441805)
17. Piispanen R, Saranpaa P (2002) Neutral lipids and phospholipids in Scots pine (Pinus sylvestris) sapwood and heartwood. Tree Physiol 22:661-666 (Pubitemid 34853415)
18. Pereira SL, Leonard AE, Mukerji P (2003) Recent advances in the study of fatty acid desaturases from animals and lower eukaryotes. Prostaglandins Leukot Essent Fatty Acids 68:97-106 (Pubitemid 36216473)
19. Sprecher H, Luthria DL, Mohammed BS, Baykousheva SP (1995) Reevaluation of the pathways for the biosynthesis of polyunsaturated fatty acids. J Lipid Res 36:2471-2477 (Pubitemid 26028787)
20. Wallis JG, Browse J (1999) The Delta8-desaturase of Euglena gracilis: an alternate pathway for synthesis of 20-carbon polyunsaturated fatty acids. Arch Biochem Biophys 365:307-316 (Pubitemid 29391640)
21. 5-fusion desaturase. FEBS Lett 580:1946-1952
22. Venegas-Caleron M, Beaudoin F, Sayanova O, Napier JA (2007) Co-transcribed genes for long chain polyunsaturated fatty acid biosynthesis in the protozoon Perkinsus marinus include a plant-like FAE1 3-ketoacyl coenzyme A synthase. J Biol Chem 282:2996-3003 (Pubitemid 47084336)
23. Reddy AS, Nuccio ML, Gross LM, Thomas TL (1993) Isolation of a delta 6-desaturase gene from the cyanobacterium Synechocystis sp. strain PCC 6803 by gain-of-function expression in Anabaena sp. strain PCC 7120. Plant Mol Biol 22:293-300
24. Deshnium P, Paithoonrangsarid K, Suphatrakul A, Meesapyodsuk D, Tanticharoen M, Cheevadhanarak S (2000) Temperatureindependent and -dependent expression of desaturase genes in filamentous cyanobacterium Spirulina platensis strain C1 (Arthrospira sp. PCC 9438). FEMS Microbiol Lett 184:207-213 (Pubitemid 30125341)
25. Thomas TL, Reddy AS, Nuccio M, Nunberg AN, Freyssinet GL (1997) Production of gamma-linolenic acid by a delta6-desaturase. U. S. Patent 4,736,866
26. Domergue F, Abbadi A, Zahringer U, Moreau H, Heinz E (2005) In vivo characterization of the first acyl-CoA Delta6-desaturase from a member of the plant kingdom, the microalga Ostreococcus tauri. Biochem J 389:483-490 (Pubitemid 41021152)
27. Hoffmann M, Wagner M, Abbadi A, Fulda M, Feussner I (2008) Metabolic engineering of omega3-very long chain polyunsaturated fatty acid production by an exclusively acyl-CoA-dependent pathway. J Biol Chem 283:22352-22362
28. Domergue F, Lerchl J, Zahringer U, Heinz E (2002) Cloning and functional characterization of Phaeodactylum tricornutum frontend desaturases involved in eicosapentaenoic acid biosynthesis. Eur J Biochem 269:4105-4113 (Pubitemid 34994905)
29. Girke T, Schmidt H, Zahringer U, Reski R, Heinz E (1998) Identification of a novel delta 6-acyl-group desaturase by targeted gene disruption in Physcomitrella patens. Plant J 15:39-48
30. Laoteng K, Mannontarat R, Tanticharoen M, Cheevadhanarak S (2000) Delta6-desaturase of Mucor rouxii with high similarity to plant delta 6-desaturase and its heterologous expression in Saccharomyces cerevisiae. Biochem Biophys Res Commun 279:17-22
31. Sakuradani E, Kobayashi M, Shimizu S (1999) Delta6-fatty acid desaturase from an arachidonic acid-producing Mortierella fungus. Gene cloning and its heterologous expression in a fungus, Aspergillus. Gene 238:445-453 (Pubitemid 29446179)
32. Hong H, Datla N, Reed DW, Covello PS, MacKenzie SL, Qiu X (2002) High-level production of gamma-linolenic acid in Brassica juncea using a delta6 desaturase from Pythium irregulare. Plant Physiol 129:354-362 (Pubitemid 34527333)
33. Zheng X, Tocher DR, Dickson CA, Bell JG, Teale AJ (2005) Highly unsaturated fatty acid synthesis in vertebrates: new insights with the cloning and characterization of a delta6 desaturase of Atlantic salmon. Lipids 40:13-24
34. Seiliez I, Panserat S, Kaushik S, Bergot P (2001) Cloning, tissue distribution and nutritional regulation of a Delta6-desaturaselike enzyme in rainbow trout. Comp Biochem Physiol B Biochem Mol Biol 130:83-93 (Pubitemid 32695338)
35. Cho HP, Nakamura MT, Clarke SD (1999) Cloning, expression, and nutritional regulation of the mammalian Delta-6 desaturase. J Biol Chem 274:471-477 (Pubitemid 29035085)
36. 5 fusion protein. J Biol Chem 273:28590-28596 (Pubitemid 28507541)
37. Sayanova O, Beaudoin F, Libisch B, Castel A, Shewry PR, Napier JA (2001) Mutagenesis and heterologous expression in yeast of a plant Delta6-fatty acid desaturase. J Exp Bot 52:1581-1585 (Pubitemid 32686381)
38. Sayanova OV, Beaudoin F, Michaelson LV, Shewry PR, Napier JA (2003) Identification of primula fatty acid delta 6-desaturases with n-3 substrate preferences. FEBS Lett 542:100-104 (Pubitemid 36555722)
39. 5 superfamily. Eur J Biochem 267:3801-3811 (Pubitemid 30423043)
40. de Antueno RJ, Knickle LC, Smith H, Elliot ML, Allen SJ, Nwaka S, Winther MD (2001) Activity of human Delta5 and Delta6 desaturases on multiple n-3 and n-6 polyunsaturated fatty acids. FEBS Lett 509:77-80 (Pubitemid 33153084)
41. Reddy AS, Thomas TL (1996) Expression of a cyanobacterial delta 6-desaturase gene results in gamma-linolenic acid production in transgenic plants. Nat Biotechnol 14:639-642
42. Truksa M, Vrinten P, Qiu X (2008) Metabolic engineering of plants for polyunsaturated fatty acid production. Mol Breed 23:1-11
43. Liu JW, Huang YS, DeMichele S, Bergana M, E Jr Bobik, Hastilow C, Chuang LT, Mukerji P, Knutzon D (2001) Evaluation of the seed oils from a canola plant genetically transformed to produce high levels of gamma-linolenic acid. In: Huang YS, Ziboh VA (eds) Gamma-linolenic acid: recent advances in biotechnology and clinical applications. AOCS Press, Champaign, IL, pp 61-71
44. Ursin VM (2003) Modification of plant lipids for human health: development of functional land-based omega-3 fatty acids. J Nutr 133:4271-4274 (Pubitemid 37505514)
45. Eckert H, La VB, Schweiger BJ, Kinney AJ, Cahoon EB, Clemente T (2006) Co-expression of the borage Delta 6 desaturase and the Arabidopsis Delta 15 desaturase results in high accumulation of stearidonic acid in the seeds of transgenic soybean. Planta 224:1050-1057 (Pubitemid 44435856)
46. Knauf VC, Shewmaker C, Flider F, Emlay D, Rey E (2011) Safflower with elevated gamma-linolenic acid. U. S. Patent 7,893,321B2
47. Knutzon DS, Thurmond JM, Huang YS, Chaudhary S, Bobik EG Jr, Chan GM, Kirchner SJ, Mukerji P (1998) Identification of Delta5-desaturase from Mortierella alpina by heterologous expression in bakers' yeast and canola. J Biol Chem 273:29360-29366 (Pubitemid 28509935)
48. Michaelson LV, Lazarus CM, Griffiths G, Napier JA, Stobart AK (1998) Isolation of a Delta5-fatty acid desaturase gene from Mortierella alpina. J Biol Chem 273:19055-19059 (Pubitemid 28366298)
49. Kajikawa M, Matsui K, Ochiai M, Tanaka Y, Kita Y, Ishimoto M, Kohzu Y, Shoji S, Yamato KT, Ohyama K, Fukuzawa H, Kohchi T (2008) Production of arachidonic and eicosapentaenoic acids in plants using bryophyte fatty acid Delta6-desaturase, Delta6-elongase, and Delta5-desaturase genes. Biosci Biotechnol Biochem 72:435-444 (Pubitemid 351353656)
50. Kajikawa M, Yamato KT, Kohzu Y, Nojiri M, Sakuradani E, Shimizu S, Sakai Y, Fukuzawa H, Ohyama K (2004) Isolation and characterization of delta (6)-desaturase, an ELO-like enzyme and delta (5)-desaturase from the liverwort Marchantia polymorpha and production of arachidonic and eicosapentaenoic acids in the methylotrophic yeast Pichia pastoris. Plant Mol Biol 54:335-352 (Pubitemid 39059561)
51. Saito T, Ochiai H (1999) Identification of Delta5-fatty acid desaturase from the cellular slime mold Dictyostelium discoideum. Eur J Biochem 265:809-814 (Pubitemid 29489014)
52. Cho HP, Nakamura M, Clarke SD (1999) Cloning, expression, and fatty acid regulation of the human delta-5 desaturase. J Biol Chem 274:37335-37339
53. Hong H, Datla N, MacKenzie SL, Qiu X (2002) Isolation and characterization of a delta5 FA desaturase from Pythium irregulare by heterologous expression in Saccharomyces cerevisiae and oilseed crops. Lipids 37:863-868 (Pubitemid 35332924)
54. Kaewsuwan S, Cahoon EB, Perroud PF, Wiwat C, Panvisavas N, Quatrano RS, Cove DJ, Bunyapraphatsara N (2006) Identification and functional characterization of the moss Physcomitrella patens delta5-desaturase gene involved in arachidonic and eicosapentaenoic acid biosynthesis. J Biol Chem 281:21988-21997 (Pubitemid 44181902)
55. Tavares S, Grotkjaer T, Obsen T, Haslam RP, Napier JA, Gunnarsson N (2011) Metabolic engineering of Saccharomyces cerevisiae for production of eicosapentaenoic acid, using a novel {Delta}5-desaturase from Paramecium tetraurelia. Appl Environ Microbiol 77:1854-1861
56. Tonon T, Sayanova O, Michaelson LV, Qing R, Harvey D, Larson TR, Li Y, Napier JA, Graham IA (2005) Fatty acid desaturases from the microalga Thalassiosira pseudonana. FEBS J 272:3401-3412 (Pubitemid 40979310)
57. Hastings N, Agaba M, Tocher DR, Leaver MJ, Dick JR, Sargent JR, Teale AJ (2001) A vertebrate fatty acid desaturase with Delta 5 and Delta 6 activities. Proc Natl Acad Sci USA 98:14304-14309 (Pubitemid 33121387)
58. Abbadi A, Domergue F, Bauer J, Napier JA, Welti R, Zahringer U, Cirpus P, Heinz E (2004) Biosynthesis of very-long-chain polyunsaturated fatty acids in transgenic oilseeds: constraints on their accumulation. Plant Cell 16:2734-2748
59. Cheng B, Wu G, Vrinten P, Falk K, Bauer J, Qiu X (2010) Towards the production of high levels of eicosapentaenoic acid in transgenic plants: the effects of different host species, genes and promoters. Transgenic Res 19:221-229
60. Voss A, Reinhart M, Sankarappa S, Sprecher H (1991) The metabolism of 7, 10, 13, 16, 19-docosapentaenoic acid to 4, 7, 10, 13, 16, 19-docosahexaenoic acid in rat liver is independent of a 4-desaturase J Biol Chem 266:19995-20000 (Pubitemid 21908418)
61. Meyer A, Cirpus P, Ott C, Schlecker R, Zahringer U, Heinz E (2003) Biosynthesis of docosahexaenoic acid in Euglena gracilis: biochemical and molecular evidence for the involvement of a Delta4-fatty acyl group desaturase. Biochemistry 42:9779-9788 (Pubitemid 36993151)
62. Tripodi KE, Buttigliero LV, Altabe SG, Uttaro AD (2006) Functional characterization of front-end desaturases from trypanosomatids depicts the first polyunsaturated fatty acid biosynthetic pathway from a parasitic protozoan. FEBS J 273:271-280
63. Tonon T, Harvey D, Larson TR, Graham IA (2003) Identification of a very long chain polyunsaturated fatty acid Delta4-desaturase from the microalga Pavlova lutheri. FEBS Lett 553:440-444 (Pubitemid 37315646)
64. Zhou XR, Robert SS, Petrie JR, Frampton DM, Mansour MP, Blackburn SI, Nichols PD, Green AG, Singh SP (2007) Isolation and characterization of genes from the marine microalga Pavlova salina encoding three front-end desaturases involved in docosahexaenoic acid biosynthesis. Phytochemistry 68:785-796 (Pubitemid 46330452)
65. Li Y, Monroig O, Zhang L, Wang S, Zheng X, Dick JR, You C, Tocher DR (2010) Vertebrate fatty acyl desaturase with Delta4 activity. Proc Natl Acad Sci USA 107:16840-16845
66. Kinney AJ, Cahoon EB, Damude HG, Hitz WD, Kolar CW, Liu ZB (2004) Production of very long chain polyunsaturated fatty acids in oilseed plants. WO 2004/071467
67. Wu G, Truksa M, Datla N, Vrinten P, Bauer J, Zank T, Cirpus P, Heinz E, Qiu X (2005) Stepwise engineering to produce high yields of very long-chain polyunsaturated fatty acids in plants. Nat Biotechnol 23:1013-1017 (Pubitemid 41114037)
68. Robert SS, Singh SP, Zhou X, Petrie JR, Blackburn SI, Mansour PM, Nichols PD, Liu Q, Green AG (2005) Metabolic engineering of Arabidopsis to produce nutritionally important DHA in seed oil. Funct Plant Biol 32:473-479 (Pubitemid 40995784)
69. Qi B, Fraser TC, Bleakley CL, Shaw EM, Stobart AK, Lazarus CM (2003) The variant 'his-box' of the C18-Delta9-PUFA-specific elongase IgASE1 from Isochrysis galbana is essential for optimum enzyme activity. FEBS Lett 547:137-139 (Pubitemid 36829393)
70. Park WJ, Kothapalli KS, Lawrence P, Tyburczy C, Brenna JT (2009) An alternate pathway to long-chain polyunsaturates: the FADS2 gene product Delta8-desaturates 20:2n-6 and 20:3n-3. J Lipid Res 50:1195-1202
71. Sayanova O, Haslam RP, Caleron MV, Lopez NR, Worthy C, Rooks P, Allen MJ, Napier JA (2011) Identification and functional characterisation of genes encoding the omega-3 polyunsaturated fatty acid biosynthetic pathway from the coccolithophore Emiliania huxleyi. Phytochemistry 72:594-600
72. Qi B, Fraser T, Mugford S, Dobson G, Sayanova O, Butler J, Napier JA, Stobart AK, Lazarus CM (2004) Production of very long chain polyunsaturated omega-3 and omega-6 fatty acids in plants. Nat Biotechnol 22:739-745 (Pubitemid 38702831)
73. Petrie JR, Shrestha P, Belide S, Mansour MP, Liu Q, Horne J, Nichols PD, Singh SP (2011) Transgenic production of arachidonic acid in oilseeds. Transgenic Res. doi:10.1007/s11248-011-9517-7
74. Shanklin J, Somerville C (1991) Stearoyl-acyl-carrier-protein desaturase from higher plants is structurally unrelated to the animal and fungal homologs. Proc Natl Acad Sci USA 88:2510-2514 (Pubitemid 21916447)
75. Stymne S, Stobart AK (1986) Biosynthesis of gamma-linolenic acid in cotyledons and microsomal preparations of the developing seeds of common borage (Borago officinalis). Biochem J 240:385-393
76. Griffiths G, Stobart AK, Stymne S (1988) Delta 6-and delta 12-desaturase activities and phosphatidic acid formation in microsomal preparations from the developing cotyledons of common borage (Borago officinalis). Biochem J 252:641-647
77. Domergue F, Abbadi A, Ott C, Zank TK, Zahringer U, Heinz E (2003) Acyl carriers used as substrates by the desaturases and elongases involved in very long-chain polyunsaturated fatty acids biosynthesis reconstituted in yeast. J Biol Chem 278:35115-35126 (Pubitemid 37102275)
78. Petrie JR, Shrestha P, Mansour MP, Nichols PD, Liu Q, Singh SP (2010) Metabolic engineering of omega-3 long-chain polyunsaturated fatty acids in plants using an acyl-CoA Delta6-desaturase with omega3-preference from the marine microalga Micromonas pusilla. Metab Eng 12:233-240
79. Sperling P, Ternes P, Zank TK, Heinz E (2003) The evolution of desaturases. Prostaglandins Leukot Essent Fatty Acids 68:73-95 (Pubitemid 36216472)
80. Stukey JE, McDonough VM, Martin CE (1989) Isolation and characterization of OLE1, a gene affecting fatty acid desaturation from Saccharomyces cerevisiae. J Biol Chem 264:16537-16544 (Pubitemid 19243545)
81. 5-like domain is linked to the carboxyl terminus of the Saccharomyces cerevisiae delta-9 fatty acid desaturase. J Biol Chem 270:29766-29772
82. Qiu X, Hong H, Datla N, MacKenzie SL, Taylor DC, Thomas TL (2002) Expression of borage delta-6 desaturase in Saccharomyces cerevisiae and oilseed crops. Can J Bot 80:42-49 (Pubitemid 34190511)
83. Hongsthong A, Subudhi S, Sirijuntarut M, Kurdrid P, Cheevadhanarak S, Tanticharoen M (2006) Revealing the complementation of ferredoxin by cytochrome b (5) in the Spirulina-(6)-desaturation reaction by N-terminal fusion and co-expression of the fungalcytochrome b (5) domain and Spirulina-(6)-acyl-lipid desaturase. Appl Microbiol Biotechnol 72:1192-1201 (Pubitemid 44564454)
84. Sayanova O, Shewry PR, Napier JA (1999) Histidine-41 of the cytochrome b5 domain of the borage delta6 fatty acid desaturase is essential for enzyme activity. Plant Physiol 121:641-646 (Pubitemid 29498926)
85. Na-Ranong S, Laoteng K, Kittakoop P, Tanticharoen M, Cheevadhanarak S (2006) Targeted mutagenesis of a fatty acid Delta6-desaturase from Mucor rouxii: role of amino acid residues adjacent to histidine-rich motif II. Biochem Biophys Res Commun 339:1029-1034 (Pubitemid 41790567)
86. Libisch B, Michaelson LV, Lewis MJ, Shewry PR, Napier JA (2000) Chimeras of Delta6-fatty acid and Delta8-sphingolipid desaturases. Biochem Biophys Res Commun 279:779-785 (Pubitemid 32043609)
87. Lange SJ, Que L Jr (1998) Oxygen activating nonheme iron enzymes. Curr Opin Chem Biol 2:159-172 (Pubitemid 128428123)
88. Shanklin J, Guy JE, Mishra G, Lindqvist Y (2009) Desaturases: emerging models for understanding functional diversification of diiron-containing enzymes. J Biol Chem 284:18559-18563
89. Whyte LG, Schultz A, Beilen JB, Luz AP, Pellizari V, Labbe D, Greer CW (2002) Prevalence of alkane monooxygenase genes in Arctic and Antarctic hydrocarbon-contaminated and pristine soils. FEMS Microbiol Ecol 41:141-150 (Pubitemid 34880052)
90. Feussner I, Wasternack C, Kindl H, Kuhn H (1995) Lipoxygenase-catalyzed oxygenation of storage lipids is implicated in lipid mobilization during germination. Proc Natl Acad Sci USA 92:11849-11853 (Pubitemid 26014207)
91. Arciero DM, Orville AM, Lipscomb JD (1985) [17O]Water and nitric oxide binding by protocatechuate 4, 5-dioxygenase and catechol 2, 3-dioxygenase. Evidence for binding of exogenous ligands to the active site Fe2+ of extradiol dioxygenases. J Biol Chem 260:14035-14044 (Pubitemid 16194608)
92. Shanklin J, Whittle E, Fox BG (1994) Eight histidine residues are catalytically essential in a membrane-associated iron enzyme, stearoyl-CoA desaturase, and are conserved in alkane hydroxylase and xylene monooxygenase. Biochemistry 33:12787-12794 (Pubitemid 24352868)
93. Fauconnot L, Buist PH (2001) Gamma-linolenic acid biosynthesis: cryptoregiochemistry of delta6 desaturation. J Org Chem 66:1210-1215 (Pubitemid 32202303)
94. Behrouzian B, Buist PH (2003) Mechanism of fatty acid desaturation: a bioorganic perspective. Prostaglandins Leukot Essent Fatty Acids 68:107-112 (Pubitemid 36216474)
95. Meesapyodsuk D, Reed DW, Savile CK, Buist PH, Schafer UA, Ambrose SJ, Covello PS (2000) Substrate specificity, regioselectivity and cryptoregiochemistry of plant and animal omega-3 fatty acid desaturases. Biochem Soc Trans 28:632-635 (Pubitemid 32163212)
96. Aguilar PS, de MD (2006) Control of fatty acid desaturation: a mechanism conserved from bacteria to humans. Mol Microbiol 62:1507-1514 (Pubitemid 44813799)
97. Napier JA (2007) The production of unusual fatty acids in transgenic plants. Annu Rev Plant Biol 58:295-319 (Pubitemid 46986327)
98. Sayanova O, Napier JA (2011) Transgenic oilseed crops as an alternative to fish oils. Prostaglandins Leukot Essent Fatty Acids 85:253-260
99. Singh SP, Zhou XR, Liu Q, Stymne S, Green AG (2005) Metabolic engineering of new fatty acids in plants. Curr Opin Plant Biol 8:197-203 (Pubitemid 40323550)
100. Napier JA, Graham IA (2010) Tailoring plant lipid composition: designer oilseeds come of age. Curr Opin Plant Biol 13:330-337
101. Graham IA, Larson T, Napier JA (2007) Rational metabolic engineering of transgenic plants for biosynthesis of omega-3 polyunsaturates. Curr Opin Biotechnol 18:142-147 (Pubitemid 46575226)
102. Cahoon EB, Shockey JM, Dietrich CR, Gidda SK, Mullen RT, Dyer JM (2007) Engineering oilseeds for sustainable production of industrial and nutritional feedstocks: solving bottlenecks in fatty acid flux. Curr Opin Plant Biol 10:236-244 (Pubitemid 46710478)