Remote control of regioselectivity in acyl-acyl carrier protein-desaturases

Proceedings of the National Academy of Sciences of the United States of America

Volumn 108, Issue 40, 2011, Pages 16594-16599

  Guy, Jodie E ^a   Whittle, Edward ^b   Moche, Martin ^a   Lengqvist, Johan ^a,c   Lindqvist, Ylva ^a   Shanklin, John ^b  

^a KAROLINSKA INSTITUTE   (Sweden)

^b BROOKHAVEN NATIONAL LABORATORY   (United States)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

Diiron enzyme; Enzyme mechanism; Enzyme redesign; Lipid metabolism

Indexed keywords

3 OXOACYL ACYL CARRIER PROTEIN SYNTHASE; ACYL CARRIER PROTEIN; ACYL COENZYME A DESATURASE; CASTOR OIL; PANTETHEINE PHOSPHATE;

ARTICLE; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME SYNTHESIS; FATTY ACID DESATURATION; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

ACYL CARRIER PROTEIN; CRYSTALLIZATION; FATTY ACID DESATURASES; FATTY ACIDS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MUTAGENESIS; PROTEIN CONFORMATION; SUBSTRATE SPECIFICITY;

HEDERA;

EID: 80053651576     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1110221108     Document Type: Article

References (34)

1. Bloch K (1969) Enzymatic synthesis of monounsaturated fatty acids. Acc Chem Res 2:193-202.
2. Shanklin J, Cahoon EB (1998) Desaturation and related modifications of fatty acids. Annu Rev Plant Physiol Plant Mol Biol 49:611-641.
3. Shanklin J (2000) Exploring the possibilities presented by protein engineering. Curr Opin Plant Biol 3:243-248.
4. 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)
5. Lindqvist Y, Huang W, Schneider G, Shanklin J (1996) Crystal structure of a delta nine stearoyl-acyl carrier protein desaturase from castor seed and its relationship to other diiron proteins. EMBO J 15:4081-4092. (Pubitemid 26278691)
6. Behrouzian B, Savile CK, Dawson B, Buist PH, Shanklin J (2002) Exploring the hydroxylation- dehydrogenation connection: Novel catalytic activity of castor stearoyl-ACP Delta(9) desaturase. J Am Chem Soc 124:3277-3283. (Pubitemid 34270367)
7. Guy JE, Whittle E, Kumaran D, Lindqvist Y, Shanklin J (2007) The crystal structure of the ivy Delta4-16:0-ACP desaturase reveals structural details of the oxidized active site and potential determinants of regioselectivity. J Biol Chem 282:19863-19871. (Pubitemid 47100091)
8. Whittle E, Cahoon EB, Subrahmanyam S, Shanklin J (2005) A multifunctional acyl-acyl carrier protein desaturase from Hedera helix L. (English ivy) can synthesize 16- and 18-carbon monoene and diene products. J Biol Chem 280:28169-28176. (Pubitemid 41105712)
9. Broadwater JA, Ai J, Loehr TM, Sanders-Loehr J, Fox BG (1998) Peroxodiferric intermediate of stearoyl-acyl carrier protein delta 9 desaturase: Oxidase reactivity during single turnover and implications for the mechanism of desaturation. Biochemistry 37:14664-14671. (Pubitemid 28487574)
10. Haas JA, Fox BG (2002) Fluorescence anisotropy studies of enzyme-substrate complex formation in stearoyl-ACP desaturase. Biochemistry 41:14472-14481. (Pubitemid 35440258)
11. Moche M, Shanklin J, Ghoshal A, Lindqvist Y (2003) Azide and acetate complexes plus two iron-depleted crystal structures of the di-iron enzyme delta9 stearoyl-acyl carrier protein desaturase. Implications for oxygen activation and catalytic intermediates. J Biol Chem 278:25072-25080. (Pubitemid 37548671)
12. Holm L, Rosenstrom P (2010) Dali server: Conservation mapping in 3D. Nucleic Acids Res 38:W545-549.
13. Krissinel E, Henrick K (2007) Inference of macromolecular assemblies from crystalline state. J Mol Biol 372:774-797. (Pubitemid 47321791)
14. de Vries SJ, van Dijk M, Bonvin AM The HADDOCK web server for data-driven biomolecular docking. Nat Protoc 5:883-897.
15. Tremblay AE, Whittle E, Buist PH, Shanklin J (2007) Stereochemistry of Delta4 dehydrogenation catalyzed by an ivy (Hedera helix) Delta9 desaturase homolog. Org Biomol Chem 5:1270-1275. (Pubitemid 46543585)
16. Heilmann I, Pidkowich MS, Girke T, Shanklin J (2004) Switching desaturase enzyme specificity by alternate subcellular targeting. Proc Natl Acad Sci USA 101:10266-10271. (Pubitemid 38924914)
17. Nguyen HT, et al. (2010) Metabolic engineering of seeds can achieve levels of omega-7 fatty acids comparable with the highest levels found in natural plant sources. Plant Physiol 154:1897-1904.
18. 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. (Pubitemid 27214703)
19. Shanklin J (2000) Overexpression and purification of the Escherichia coli inner membrane enzyme acyl-acyl carrier protein synthase in an active form. Protein Expr Purif 18:355-360 and correction (2000) 19:319.
20. Leslie AG (1992) Recent changes to the MOSFLM package for processing film and image plate data. Joint CCP4 + ESF-EAMCB Newsletter on Protein Crystallography, 26.
21. Evans PR (1993) Data Collection and Processing (Daresbury Lab, Warrington, UK), pp 114-122.
22. Winn MD, et al. (2011) Overview of the CCP4 suite and current developments. Acta Crystallogr D Biol Crystallogr 67:235-242.
23. Vagin A, Teplyakov A (1997) Molrep: An automated program for molecular replacement. J Appl Crystallogr 30:1022-1025. (Pubitemid 127485985)
24. Murshudov GN, Vagin AA, Dodson EJ (1997) Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr 53:240-255. (Pubitemid 27235885)
25. Brunger AT, et al. (1998) Crystallography & NMR system: A new software suite for macromolecular structure determination. Acta Crystallogr D Biol Crystallogr 54:905-921.
26. Emsley P, Lohkamp B, Scott WG, Cowtan K (2010) Features and development of Coot. Acta Crystallogr D Biol Crystallogr 66:486-501.
27. Laskowski RA, MacArthur MW, Moss DS, Thornton JM (1993) PROCHECK: A program to check the stereochemical quality of protein structures. J Appl Crystallogr 26:283-291.
28. Vaguine AA, Richelle J, Wodak SJ (1999) SFCHECK: A unified set of procedures for evaluating the quality of macromolecular structure-factor data and their agreement with the atomic model. Acta Crystallogr D Biol Crystallogr 55:191-205. (Pubitemid 29053816)
29. Davis IW, et al. (2007) MolProbity: All-atom contacts and structure validation for proteins and nucleic acids. Nucleic Acids Res 35:W375-383.
30. DeLano WL (2002) The PyMOL Molecular Graphics System (DeLano Scientific, San Carlos, CA).
31. Whittle EJ, Tremblay AE, Buist PH, Shanklin J (2008) Revealing the catalytic potential of an acyl-ACP desaturase: Tandem selective oxidation of saturated fatty acids. Proc Natl Acad Sci USA 105:14738-14743.
32. Broadwater JA, Fox BG (1999) Spinach holo-acyl carrier protein: Overproduction and phosphopantetheinylation in Escherichia coli BL21(DE3), in vitro acylation, and enzymatic desaturation of histidine-tagged isoform I. Protein Expr Purif 15:314-326. (Pubitemid 29326379)
33. Cahoon EB, Shanklin J (2000) Substrate-dependent mutant complementation to select fatty acid desaturase variants for metabolic engineering of plant seed oils. Proc Natl Acad Sci USA 97:12350-12355.
34. Yamamoto K, Shibahara A, Nakayama T, Kajimoto G (1991) Determination of double-bond positions in methylene-interrupted dienoic fatty acids by GC-MS as their dimethyl disulfide adducts. Chem Phys Lipids 60:39-50.