Fatty Aldehydes in Cyanobacteria Are a Metabolically Flexible Precursor for a Diversity of Biofuel Products

PLoS ONE

Volumn 8, Issue 3, 2013, Pages

  Kaiser, Brett K ^a,f   Carleton, Michael ^a   Hickman, Jason W ^a   Miller, Cameron ^a   Lawson, David ^a   Budde, Mark ^a   Warrener, Paul ^a   Paredes, Angel ^c   Mullapudi, Srinivas ^c   Navarro, Patricia ^c   Cross, Fred ^d   Roberts, James M ^b,e  

^a Matrix Genetics   (United States)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

^d ROCKEFELLER UNIVERSITY   (United States)

^e Fred Hutchinson Cancer Research Center   (United States)

^f SEATTLE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; ALDEHYDE; ALDEHYDE DEHYDROGENASE; ALKANE; CHOLESTEROL ACYLTRANSFERASE; ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADPH);

AAR GENE; ALDE GENE; ARTICLE; BACTERIAL GENE; BACTERIAL METABOLISM; BIOFUEL PRODUCTION; CELLULAR SECRETION; CONTROLLED STUDY; CYANOBACTERIUM; FATTY ACID OXIDATION; FATTY ACID SYNTHESIS; GENE OVEREXPRESSION; LIPID STORAGE; NONHUMAN; PROTEIN EXPRESSION;

ALDEHYDE DEHYDROGENASE; ALDEHYDES; BIOFUELS; CYANOBACTERIA; ENOYL-(ACYL-CARRIER PROTEIN) REDUCTASE (NADPH, B-SPECIFIC); FATTY ACIDS; GENE EXPRESSION; KINETICS; WAXES;

EID: 84874865676     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0058307     Document Type: Article

References (46)

1. Ducat DC, Way JC, Silver PA, (2011) Engineering cyanobacteria to generate high-value products. Trends Biotechnol 29: 95-103.
2. Rock CO, Jackowski S, (2002) Forty years of bacterial fatty acid synthesis. Biochem Biophys Res Commun 292: 1155-1166.
3. Peralta-Yahya PP, Keasling JD, (2010) Advanced biofuel production in microbes. Biotechnol J 5: 147-162.
4. Heath RJ, Rock CO, (1996) Inhibition of beta-ketoacyl-acyl carrier protein synthase III (FabH) by acyl-acyl carrier protein in Escherichia coli. J Biol Chem 271: 10996-11000.
5. Heath RJ, Rock CO, (1996) Regulation of fatty acid elongation and initiation by acyl-acyl carrier protein in Escherichia coli. J Biol Chem 271: 1833-1836.
6. Davis MS, Cronan JE Jr, (2001) Inhibition of Escherichia coli acetyl coenzyme A carboxylase by acyl-acyl carrier protein. J Bacteriol 183: 1499-1503.
7. Cho H, Cronan JE Jr, (1995) Defective export of a periplasmic enzyme disrupts regulation of fatty acid synthesis. J Biol Chem 270: 4216-4219.
8. Jiang P, Cronan JE Jr, (1994) Inhibition of fatty acid synthesis in Escherichia coli in the absence of phospholipid synthesis and release of inhibition by thioesterase action. J Bacteriol 176: 2814-2821.
9. Voelker TA, Davies HM, (1994) Alteration of the specificity and regulation of fatty acid synthesis of Escherichia coli by expression of a plant medium-chain acyl-acyl carrier protein thioesterase. J Bacteriol 176: 7320-7327.
10. Liu X, Sheng J, Curtiss R, 3rd (2011) Fatty acid production in genetically modified cyanobacteria. Proc Natl Acad Sci U S A 108: 6899-6904.
11. Waltermann M, Steinbuchel A, (2005) Neutral lipid bodies in prokaryotes: recent insights into structure, formation, and relationship to eukaryotic lipid depots. J Bacteriol 187: 3607-3619.
12. Kalscheuer R, Steinbuchel A, (2003) A novel bifunctional wax ester synthase/acyl-CoA:diacylglycerol acyltransferase mediates wax ester and triacylglycerol biosynthesis in Acinetobacter calcoaceticus ADP1. J Biol Chem 278: 8075-8082.
13. Steen EJ, Kang Y, Bokinsky G, Hu Z, Schirmer A, et al. (2010) Microbial production of fatty-acid-derived fuels and chemicals from plant biomass. Nature 463: 559-562.
14. Cheng JB, Russell DW, (2004) Mammalian wax biosynthesis. I. Identification of two fatty acyl-Coenzyme A reductases with different substrate specificities and tissue distributions. J Biol Chem 279: 37789-37797.
15. Metz JG, Pollard MR, Anderson L, Hayes TR, Lassner MW, (2000) Purification of a jojoba embryo fatty acyl-coenzyme A reductase and expression of its cDNA in high erucic acid rapeseed. Plant Physiol 122: 635-644.
16. Reiser S, Somerville C, (1997) Isolation of mutants of Acinetobacter calcoaceticus deficient in wax ester synthesis and complementation of one mutation with a gene encoding a fatty acyl coenzyme A reductase. J Bacteriol 179: 2969-2975.
17. Kaczmarzyk D, Fulda M, (2010) Fatty acid activation in cyanobacteria mediated by acyl-acyl carrier protein synthetase enables fatty acid recycling. Plant Physiol 152: 1598-1610.
18. Schirmer A, Rude MA, Li X, Popova E, del Cardayre SB, (2010) Microbial biosynthesis of alkanes. Science 329: 559-562.
19. Winters K, Parker PL, Van Baalen C, (1969) Hydrocarbons of blue-green algae: geochemical signfficance. Science 163: 467-468.
20. Eser BE, Das D, Han J, Jones PR, Marsh EN, (2011) Oxygen-independent alkane formation by non-heme iron-dependent cyanobacterial aldehyde decarbonylase: investigation of kinetics and requirement for an external electron donor. Biochemistry 50: 10743-10750.
21. Li N, Norgaard H, Warui DM, Booker SJ, Krebs C, et al. (2011) Conversion of fatty aldehydes to alka(e)nes and formate by a cyanobacterial aldehyde decarbonylase: cryptic redox by an unusual dimetal oxygenase. J Am Chem Soc 133: 6158-6161.
22. Warui DM, Li N, Norgaard H, Krebs C, Bollinger JM Jr, et al. (2011) Detection of formate, rather than carbon monoxide, as the stoichiometric coproduct in conversion of fatty aldehydes to alkanes by a cyanobacterial aldehyde decarbonylase. J Am Chem Soc 133: 3316-3319.
23. Li N, Chang WC, Warui DM, Booker SJ, Krebs C, et al. (2012) Evidence for Only Oxygenative Cleavage of Aldehydes to Alk(a/e)nes and Formate by Cyanobacterial Aldehyde Decarbonylases. Biochemistry 51: 7908-7916.
24. Kelson TL, Secor McVoyJR, Rizzo WB, (1997) Human liver fatty aldehyde dehydrogenase: microsomal localization, purification, and biochemical characterization. Biochim Biophys Acta 1335: 99-110.
25. Kok M, Oldenhuis R, van der Linden MP, Meulenberg CH, Kingma J, et al. (1989) The Pseudomonas oleovorans alkBAC operon encodes two structurally related rubredoxins and an aldehyde dehydrogenase. J Biol Chem 264: 5442-5451.
26. Lindahl R, Petersen DR, (1991) Lipid aldehyde oxidation as a physiological role for class 3 aldehyde dehydrogenases. Biochem Pharmacol 41: 1583-1587.
27. Liu ZJ, Sun YJ, Rose J, Chung YJ, Hsiao CD, et al. (1997) The first structure of an aldehyde dehydrogenase reveals novel interactions between NAD and the Rossmann fold. Nat Struct Biol 4: 317-326.
28. Achterholt S, Priefert H, Steinbuchel A, (1998) Purification and characterization of the coniferyl aldehyde dehydrogenase from Pseudomonas sp. Strain HR199 and molecular characterization of the gene. J Bacteriol 180: 4387-4391.
29. Vidal R, Lopez-Maury L, Guerrero MG, Florencio FJ, (2009) Characterization of an alcohol dehydrogenase from the Cyanobacterium Synechocystis sp. strain PCC 6803 that responds to environmental stress conditions via the Hik34-Rre1 two-component system. J Bacteriol 191: 4383-4391.
30. Perozich J, Nicholas H, Wang BC, Lindahl R, Hempel J, (1999) Relationships within the aldehyde dehydrogenase extended family. Protein Sci 8: 137-146.
31. Mitchell DY, Petersen DR, (1987) The oxidation of alpha-beta unsaturated aldehydic products of lipid peroxidation by rat liver aldehyde dehydrogenases. Toxicol Appl Pharmacol 87: 403-410.
32. Nakayasu H, Mihara K, Sato R, (1978) Purification and properties of a membrane-bound aldehyde dehydrogenase from rat liver microsomes. Biochem Biophys Res Commun 83: 697-703.
33. Kotchoni SO, Kuhns C, Ditzer A, Kirch HH, Bartels D, (2006) Over-expression of different aldehyde dehydrogenase genes in Arabidopsis thaliana confers tolerance to abiotic stress and protects plants against lipid peroxidation and oxidative stress. Plant Cell Environ 29: 1033-1048.
34. De Laurenzi V, Rogers GR, Hamrock DJ, Marekov LN, Steinert PM, et al. (1996) Sjogren-Larsson syndrome is caused by mutations in the fatty aldehyde dehydrogenase gene. Nat Genet 12: 52-57.
35. Kirch HH, Nair A, Bartels D, (2001) Novel ABA- and dehydration-inducible aldehyde dehydrogenase genes isolated from the resurrection plant Craterostigma plantagineum and Arabidopsis thaliana. Plant J 28: 555-567.
36. Sheehan J, Dunahay T, Benemann J, Roessler P (1998) A look back at the US Department of energy's aquatic species program-:biodiesel from algae. National Renewable Energy Laboratory.
37. Robertson DE, Jacobson SA, Morgan F, Berry D, Church GM, et al. (2011) A new dawn for industrial photosynthesis. Photosynth Res 107: 269-277.
38. Chisti Y, (2007) Biodiesel from microalgae. Biotechnol Adv 25: 294-306.
39. Kaiser BK, Stoddard BL, (2012) DNA recognition and transcriptional regulation by the WhiA sporulation factor. Sci Rep 1: 156.
40. Bustos SA, Golden SS, (1991) Expression of the psbDII gene in Synechococcus sp. strain PCC 7942 requires sequences downstream of the transcription start site. J Bacteriol 173: 7525-7533.
41. Golden SS, Brusslan J, Haselkorn R, (1987) Genetic engineering of the cyanobacterial chromosome. Methods Enzymol 153: 215-231.
42. Andersson CR, Tsinoremas NF, Shelton J, Lebedeva NV, Yarrow J, et al. (2000) Application of bioluminescence to the study of circadian rhythms in cyanobacteria. Methods Enzymol 305: 527-542.
43. Holtman CK, Chen Y, Sandoval P, Gonzales A, Nalty MS, et al. (2005) High-throughput functional analysis of the Synechococcus elongatus PCC 7942 genome. DNA Res 12: 103-115.
44. Bligh EG, Dyer WJ, (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37: 911-917.
45. Folch J, Lees M, Sloane Stanley GH, (1957) A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem 226: 497-509.
46. Bozzola JJ, Russell LD (1992) Electron Microscopy: Principles and Techniques for Biologists: Jones and Bartlett Publishers.