Bioorganic chemistry of plant lipid desaturation

Phytochemistry Reviews

Volumn 2, Issue 1-2, 2003, Pages 103-111

  Behrouzian, B ^a,b   Buist, P H ^a  

^a CARLETON UNIVERSITY   (Canada)

^b R and D Project Development and Management   (United States)

Author keywords

Desaturase; Hydroxylase; Kinetic isotope effects; Lipids; Oxidation

Indexed keywords

ACYL CARRIER PROTEIN; FATTY ACID; LINOLEIC ACID; LIPID; OLEIC ACID;

BIOSYNTHESIS; BIOTRANSFORMATION; CHEMICAL REACTION KINETICS; CONFERENCE PAPER; DEHYDROGENATION; ENZYME ACTIVATION; ENZYME ANALYSIS; FATTY ACID DESATURATION; ISOTOPE LABELING; LIPOGENESIS; ORGANIC CHEMISTRY; OXIDATION; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN EXPRESSION; STEREOCHEMISTRY;

EID: 1642290027     PISSN: 15687767     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:PHYT.0000004179.31385.0a     Document Type: Conference Paper

References (66)

1. 9 desaturase that transforms (E)-11-tetradecenoic acid into (Z,E)-9,11- tetradecadienoic acid. Angew. Chem. Int. Ed. 39: 3279-3281.
2. Baenziger JE, Smith ICP & Hill RJ (1990) Biosynthesis and characterization of a series of deuterated cis, cis-octadeca-6,9-dienoic acids. J. Chem. Phys. Lipids 54: 17-23.
3. 8-Sphingolipid Desaturase from Higher Plants: A stereochemical and mechanistic Study on the origin of E,Z isomers. Angew. Chem. Int. Ed. 41: 2298-2300.
4. 9 desaturase. J. Chem. Soc. Chem. Commun. 401-102.
5. Behrouzian B, Fauconnot L, Daligault F, Nugier-Chauvin C, Patin H & Buist PH (2001b) Mechanism of fatty acid desaturation in the green alga Chlorella vulgaris. Eur. J. Biochem. 268: 3545-3549.
6. 19F NMR to probe enzymatic oxidation of fluorine-tagged Sulfides. Mag. Res. Chem. 40: 524-528.
7. 2HNMR Spectroscop. Chem. 2: 425-31.
8. Broadwater JA, Fox BG & Haas JA (1998) The fundamental, versatile role of diiron enzymes in lipid metabolism. Fett/Lipid 100: 103-113.
9. Broadwater JA, Whittle E & Shanklin, J (2002) Desaturation and hydroxylation. Residues 148 and 324 of Arabidopsis FAD2, in addition to substrate chain length, exert a major influence in partitioning of catalytic specificity. J. Biol. Chem. 277: 15613-15620.
10. Broun P, Shanklin J, Whittle E & Somerville C (1998) Catalyic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science 282: 1315-1317.
11. 9 desaturation. J. Am. Chem. Soc. 118: 6295-6296.
12. 12 desaturase: A kinetic isotope effect study. J. Am. Chem. Soc. 120: 871-876.
13. Buist PH & Marecak DM (1992) Stereochemical analysis of sulfoxides obtained by diverted desaturation. J. Am. Chem. Soc. 114: 5073-5080.
14. Cahoon EB, Lindqvist Y, Schneider G, Shanklin J (1997) Redesign of soluble fatty acid desaturases from plants for altered substrate specificity and double bond position Proc. Natl Acad. Sci. USA 94: 4872-4877.
15. Cahoon EB, Carlson TJ, Ripp KG, Schweiger BJ, Cook GA, Hall SE & Kinney AJ (1999) Biosynthetic origin of conjugated double bonds:production of fatty acid components of high-value drying oils in transgenic soybean embroyos. Proc. Natl Acad. Sci. USA 96: 12935-12940.
16. Cook D, Grierson D, Jones C, Wallace A, West G & Tucker G (2002) Modification of fatty acid composition in tomato (Lycopersicon esculentum) by expression of a borage Delta(6)-desaturase. Mol. Biotech. 21: 123-128.
17. Covello PS & Reed DW (1996) Functional expression of the extraplastidial Arabidopsis thaliana oleate desaturase gene (FAD2) in Saccharomyces cerevisiae. Plant Physiol. 111: 223-226.
18. Crombie L & Holloway SJ (1985) The biosynthesis of calendic acid, octadeca-(8E, 10E, 12Z)-trienoic acid, by developing marigold seeds: origins of (E,E,Z) and (Z,E,Z) conjugated triene acids in higher plants. J. Chem. Soc. Perkin Trans. I, 2425-2434.
19. 6 Desaturase and γ-linolenic acid: A biotechnology perspective. In: Huang YS, Ziboh VA (eds) γ-Linolenic Acid: Recent Advances in Biotechnology and Clinical Applications (pp. 6-23). AOCS Press.
20. Enoch HG, Catalá A & Strittmatter P (1976) Mechanism of rat liver microsomal stearyl-CoA desaturase. Studies of the substrate specificity, enzyme-substrate interactions, and the function of lipid. J. Biol. Chem. 251: 5095-5103.
21. Fauconnot L & Buist PH (2001a) Cryptoregiochemical analysis of an unusual bacterial desaturation. Bioorg. Med. Chem. Lett. 11: 2879-2881.
22. 6 desaturation. J. Org. Chem. 66: 1210-1215.
23. Fox BG, Shanklin J, Ai J, Loehr T & Sanders-Loehr J (1994) Resonance raman evidence for an Fe-O-Fe Center in stearoyl-ACP desaturase. Primary sequence identity with other diiron-oxo proteins. 33: 112776-12786.
24. Haas JA & Fox BG (2002) Fluorescence anisotropy studies of enzyme-substrate Complex Formation in stearoyl-ACP desaturase. Biochemistry 41: 14472-14481.
25. Heinz E (1993) Biosynthesis of polyunsaturated fatty acids. In: Moore TS Jr (ed) Lipid Metabolism in Plants (pp. 33-89). CRC Press, Boca Raton.
26. Hong H, Datla N, Reed DW, Covello PS, MacKenzie SL & Qiu X (2002) High-level production of γ-linolenic acid in Brassica juncea using a Delta 6 desaturase from Pythium irregulare. Plant Physiol. 129: 354-362.
27. Lee M, Lenman M, Banas A, Bafor M, Singh S, Schweizer M, Nilsson R, Liljenberg C, Dahlqvist A, Gummeson P-O, Sjödahl S, Green A & Stymne S (1998) Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. Science 280: 915-918.
28. 9 stearoyl-acyl carrier protein desaturase from castor seed and its relationship to other di-iron proteins. EMBO J. 15: 4081-1092.
29. 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.
30. 9 fatty acid desaturase from Spirulina platensis C1 (Arthrospira sp. PCC 9438). Comp. Biochem. Physiol. Biochem. Mol. Biol. 129: 831-835.
31. Merkx M, Kopp DA, Sazinsky MH, Blazyk JL, Müller J & Lippard SJ (2001) Dioxygen activation and methane hydroxylation by soluble methane monooxygenase: A tale of two irons and three proteins. Angew. Chem. Int. Ed. 40: 2782-2807.
32. Morris LJ, Harris RV, Kelly W & James AT (1968) The stereochemistry of desaturation of long-chain fatty acids in Chlorella vulgaris. Biochem. J. 109: 673-678.
33. Nakamura MT, Cho HP, Xu J, Tang ZR & Clarke SD (2001) Metabolism and functions of highly unsaturated fatty acids: An update. Lipids 36: 961-964.
34. Napier JA & Michaelson LV (2001) Towards the production of pharmaceutical fatty acids in transgenic plants. J. Sci. Food Agricul. 81: 883-888.
35. Navarro I, Font I, Fabrias G, & Camps F (1997) Stereospecificity of the (E) and (Z)-11 Myristoyl CoA desaturase in the biosynthesis of Spodoptera littoralis sex pheromone. J. Am. Chem. Soc. 119: 11335-11336.
36. Ntambi JM & Bene H (2001) Polyunsaturated fatty acid regulation of gene expression. J. Mol. Neurosci., 16: 273-278.
37. Okuley J, Lightner J, Feldmann K, Yadav N, Lark E, Browse J (1994) Arabidopsis fad2 gene encodes the enzyme that is essential for polyunsaturated lipid synthesis. Plant Cell 6: 147-158.
38. 11-myristoyl-CoA desaturase involved in the biosynthesis of Spodoptera littoralis sex pheromone. Biochemistry 38: 15272-15277.
39. Qiu X, Reed DW, Hong H, MacKenzie SL & Covello PS (2001) Identification and analysis of a gene from Calendula officinalis encoding a fatty acid conjugase. Plant Physiol. 125: 847-855.
40. Qiu X, Hong HP, 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: 42-19.
41. Rawling BJ, Reese PB, Ramer SE & Vederas JC (1989) Comparison of fatty acid and polyketide biosynthesis: Stereochemistry of Cladosporin and oleic acid formation in Cladosporium cladosporioides. J. Am. Chem. Soc. 111: 3382-3390.
42. Reed DW, Savile CK, Qiu X, Buist PH & Covello PS (2002) Mechanism of 1,4-dehydrogenation catalyzed by a fatty acid (1,4)-desaturase of Calendula officinalis. Eur. J. Biochem. 269: 5024-5029.
43. 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.
44. Rodriguez S, Camps F & Fabriàs G (2001) Synthesis of gemdideuterated tetradecanoic acids and their use in investigating the enzymatic transformation of (Z)-11-tetradecenoic acid into (E,E)-10,12-tetradecadienoic acid. J. Org. Chem. 66: 8052-8058.
45. Rodriguez S, Clapes P, Camps F & Fabriàs G (2002) Stereospecificity of an enzymatic monoene 1,4-dehydrogenation reaction: Conversion of (Z)-11-tetradecenoic acid into (E,E)-10,12-tetradecadienoic acid. J. Org. Chem. 67: 2228-2233.
46. Rogge CE & Fox BG (2002) Desaturation, chain scission, and register shift of oxygen-substituted fatty acids during reaction with stearoyl-ACP desaturase. Biochemistry 41: 10141-10148.
47. 4 desaturase initiates substrate oxidation at C-4. J. Am. Chem. Soc. 123: 4382-1385.
48. Savile CK, Reed DW, Meesapyodsuk D, Covello PS & Buist PH (2001b) Cryptoregiochemistry of a Brassica napus fatty acid desaturase (FAD3): A kinetic isotope effect study. J. Chem. Soc. Perkins Trans. 1: 1116-1121.
49. Schroepfer GJ & Bloch K (1965) The stereospecific conversion of stearic acid to oleic acid. J. Biol. Chem. 240: 54-63.
50. Schwartzbeck JL, Jung S, Abbott AG, Mosley E, Lewis S, Pries G & Powell GL (2001) Endoplasmic oleoyl-PC desaturase references the second double bond. Phytochemistry 57: 643-652.
51. Shanklin J (2000) Exploring the possibilities presented by protein engineering. Curr. Opin. Plant Biol. 3: 243-248.
52. 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.
53. Shanklin J, Achim C, Schmidt H, Fox BG & Munck E (1997) Mossbauer studies of alkane ω-hydroxylase: Evidence for a diiron cluster in an integral membrane enzyme. Proc Nat. Acad. Sci. USA 94: 2981-2986.
54. Shanklin J & Cahoon EB (1998) Desaturation and related modifications of fatty acids. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49: 611-641.
55. Somerville CR & Bonetta D (2001) Plants as factories for technical materials . Plant Physiol. 125: 168-171.
56. Sperling P & Heinz E (2001) Desaturases fused to their electron donor. Eur. J. Lipid Sci. Technol. 103: 158-180.
57. Spychalla JP, Kinney AJ & Browse J (1997) Identification of an animal ω-3 fatty acid desaturase by heterologous expression in Arabidopsis. Proc. Natl. Acad. Sci. USA 94: 1142-1147.
58. 9 fatty acid desaturase and can be functionally replaced by the rat stearoyl-CoA desaturase gene. J. Biol. Chem. 265: 20144-20149.
59. Thelen JJ & Ohlrogge JB (2002) Metabolic engineering of fatty acid biosynthesis in plants. Metabol. Engin. 4: 12-21.
60. Van de Loo FJ, Fox BG & Somerville C (1993) Unusual Fatty Acids. In: Moore TS Jr (ed) Lipid Metabolism in Plants (pp. 33-89). CRC Press, Boca Raton.
61. Van de Loo FJ, Broun P, Turner S & Somerville C (1995) An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog. Proc. Natl. Acad. Sci. USA 92: 6743-6747.
62. Wallis JG & Browse J (2002) Mutants of Arabidopsis reveal many roles for membrane lipids. Prog. Lipid. Res. 41: 254-278.
63. Wasternack C, Miersch O, Kramel R, Hause B, Ward J, Beale M, Boland W, Parthier B & Feussner I (1998) Jasmonic acid: Biosynthesis, signal transduction, gene expression. Fett/Lipid 100: 139-146.
64. th International Conference on Bioinorganic Chemistry, August. 26-31, 2001, Florence, Italy. (Available as J. Inorg. Biochem. 86: 479.)
65. th International Conference on Bioinorganic Chemistry, August. 26-31, 2001, Florence, Italy. (Available as J. Inorg. Biochem. 86: 479.)
66. 9 - desaturase: Substrate binding and comparison to ribonucleotide reductase. J. Am. Chem. Soc. 121: 2770-2783.