fadD deletion and fadL overexpression in Escherichia coli increase hydroxy long-chain fatty acid productivity

Applied Microbiology and Biotechnology

Volumn 98, Issue 21, 2014, Pages 8917-8925

  Bae, Jin H ^a   Park, Beom Gi ^a   Jung, Eunok ^a   Lee, Pyung Gang ^a   Kim, Byung Gee ^a  

^a Seoul National University   (South Korea)

Author keywords

E. coli host strain; FadD; FadL; Hydroxy long chain fatty acid; Long chain fatty acid transport

Indexed keywords

ENZYMES; ESCHERICHIA COLI; HYDROXYLATION; PRODUCTIVITY; SATURATED FATTY ACIDS;

ACYL-COA SYNTHETASE; CATABOLITE REPRESSION; FADD; FADL; FATTY ACID METABOLISM; GENETIC MANIPULATIONS; HOST STRAIN; LONG CHAIN FATTY ACID;

PALMITIC ACID;

CYTOCHROME P450; FAS ASSOCIATED DEATH DOMAIN PROTEIN; GLUCOSE; LONG CHAIN FATTY ACID; PALMITIC ACID; ACYL-COENZYME A SYNTHETASE, E COLI; ESCHERICHIA COLI PROTEIN; FADL PROTEIN, E COLI; FATTY ACID; FATTY ACID TRANSPORTER; LONG CHAIN FATTY ACID COENZYME A LIGASE; OUTER MEMBRANE PROTEIN; RECOMBINANT PROTEIN;

BACTERIUM; ENZYME ACTIVITY; FATTY ACID; GENE EXPRESSION; GENETIC ENGINEERING; GLUCOSE; MUTATION;

ARTICLE; CARBON SOURCE; CATABOLITE REPRESSION; CONTROLLED STUDY; COSMETIC INDUSTRY; DELETION MUTANT; ELECTRON TRANSPORT; ESCHERICHIA COLI; FATTY ACID METABOLISM; FATTY ACID TRANSPORT; GAS CHROMATOGRAPHY; GENETIC MANIPULATION; HYDROXYLATION; MARINOBACTER HYDROCARBONOCLASTICUS; NONHUMAN; PSEUDOMONAS PUTIDA; QUALITATIVE ANALYSIS; SYNTHESIS; WILD TYPE; ENZYMOLOGY; GENE DELETION; GENE EXPRESSION; GENETICS; MARINOBACTER; METABOLIC ENGINEERING; METABOLISM;

ESCHERICHIA COLI; MARINOBACTER HYDROCARBONOCLASTICUS;

BACTERIAL OUTER MEMBRANE PROTEINS; COENZYME A LIGASES; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; FATTY ACID TRANSPORT PROTEINS; FATTY ACIDS; GENE DELETION; GENE EXPRESSION; MARINOBACTER; METABOLIC ENGINEERING; RECOMBINANT PROTEINS;

EID: 84919905507     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5974-2     Document Type: Article

References (39)

1. Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H (2006) Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection. Mol Syst Biol 2:2006.0008. doi:10.1038/msb4100050
2. Black PN, DiRusso CC (2003) Transmembrane movement of exogenous long-chain fatty acids: proteins, enzymes, and vectorial esterification. Microbiol Mol Biol Rev 67(3):454–472. doi:10.1128/mmbr.67.3.454-472.2003
3. Budde M, Maurer SC, Schmid RD, Urlacher VB (2004) Cloning, expression and characterisation of CYP102A2, a self-sufficient P450 monooxygenase from Bacillus subtilis. Appl Microbiol Biotechnol 66(2):180–186. doi:10.1007/s00253-004-1719-y
4. Campbell JW, Cronan JE Jr (2002) The enigmatic Escherichia coli fadE gene is yafH. J Bacteriol 184(13):3759–3764. doi:10.1128/jb.184.13.3759-3764.2002
5. Choi KY, Park HY, Kim BG (2010) Characterization of bi-functional CYP154 from Nocardia farcinica IFM10152 in the O-dealkylation and ortho-hydroxylation of formononetin. Enzym Microb Technol 47(7):327–334. doi:10.1016/j.enzmictec.2010.08.006
6. Dapurkar SE, Kawanami H, Yokoyama T, Ikushima Y (2009) Catalytic oxidation of oleic acid in supercritical carbon dioxide media with molecular oxygen. Top Catal 52(6–7):707–713. doi:10.1007/s11244-009-9212-6
7. Datsenko KA, Wanner BL (2000) One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci U S A 97(12):6640–6645. doi:10.1073/pnas.120163297
8. Faergeman NJ, Knudsen J (1997) Role of long-chain fatty acyl-CoA esters in the regulation of metabolism and in cell signaling. Biochem J 323(1):1–12
9. Feng Y, Cronan JE (2012) Crosstalk of Escherichia coli FadR with global regulators in expression of fatty acid transport genes. PLoS One 7(9):e46275. doi:10.1371/journal.pone.0046275
10. Glatz JFC, Luiken JJFP, Bonen A (2010) Membrane fatty acid transporters as regulators of lipid metabolism: implications for metabolic disease. Physiol Rev 90(1):367–417. doi:10.1152/physrev.00003.2009
11. Hearn EM, Patel DR, Lepore BW, Indic M, van den Berg B (2009) Transmembrane passage of hydrophobic compounds through a protein channel wall. Nature 458(7236):367–370. doi:10.1038/nature07678
12. Honda Malca S, Scheps D, Kuhnel L, Venegas-Venegas E, Seifert A, Nestl BM, Hauer B (2012) Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids. Chem Commun 48(42):5115–5117. doi:10.1039/c2cc18103g
13. Ingram LO (1976) Adaptation of membrane lipids to alcohols. J Bacteriol 125(2):670–678
14. Joo YC, Seo ES, Kim YS, Kim KR, Park JB, Oh DK (2012) Production of 10-hydroxystearic acid from oleic acid by whole cells of recombinant Escherichia coli containing oleate hydratase from Stenotrophomonas maltophilia. J Biotechnol 158(1–2):17–23. doi:10.1016/j.jbiotec.2012.01.002
15. Kameda K, Nunn WD (1981) Purification and characterization of acyl coenzyme A synthetase from Escherichia coli. J Biol Chem 256(11):5702–5707
16. Kampf JP, Kleinfeld AM (2007) Is membrane transport of FFA mediated by lipid, protein, or both? An unknown protein mediates free fatty acid transport across the adipocyte plasma membrane. Physiology 22:7–14. doi:10.1152/physiol.00011.2006
17. Klein K, Steinberg R, Fiethen B, Overath P (1971) Fatty acid degradation in Escherichia coli. Eur J Biochem 19(3):442–450. doi:10.1111/j.1432-1033.1971.tb01334.x
18. Labinger JA, Bercaw JE (2002) Understanding and exploiting C–H bond activation. Nature 417(6888):507–514
19. Lee SG, Lee JO, Yi JK, Kim BG (2002) Production of cytidine 5′-monophosphate N-acetylneuraminic acid using recombinant Escherichia coli as a biocatalyst. Biotechnol Bioeng 80(5):516–524. doi:10.1002/bit.10398
20. Lu W, Ness JE, Xie W, Zhang X, Minshull J, Gross RA (2010) Biosynthesis of monomers for plastics from renewable oils. J Am Chem Soc 132(43):15451–15455. doi:10.1021/ja107707v
21. Martinez E, Estupinan M, Pastor FI, Busquets M, Diaz P, Manresa A (2013) Functional characterization of ExFadLO, an outer membrane protein required for exporting oxygenated long-chain fatty acids in Pseudomonas aeruginosa. Biochimie 95(2):290–298. doi:10.1016/j.biochi.2012.09.032
22. Mizugaki M, Yonaha M, Uchiyama M, Okui S (1968) Metabolism of hydroxy fatty acids: VI. Structure of hydroxy acids and the degradation by Escherichia coli K-12. J Biochem 63(3):390–394
23. Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver microsomes: I. Evidence for its hemoprotein nature. J Biol Chem 239(7):2370–2378
24. Pauli G, Ehring R, Overath P (1974) Fatty acid degradation in Escherichia coli: requirement of cyclic adenosine monophosphate and cyclic adenosine monophosphate receptor protein for enzyme synthesis. J Bacteriol 117(3):1178–1183
25. Pech-Canul A, Nogales J, Miranda-Molina A, Alvarez L, Geiger O, Soto MJ, Lopez-Lara IM (2011) FadD is required for utilization of endogenous fatty acids released from membrane lipids. J Bacteriol 193(22):6295–6304. doi:10.1128/JB.05450-11
26. Rude MA, Baron TS, Brubaker S, Alibhai M, Del Cardayre SB, Schirmer A (2011) Terminal olefin (1-alkene) biosynthesis by a novel P450 fatty acid decarboxylase from Jeotgalicoccus species. Appl Environ Microbiol 77(5):1718–1727. doi:10.1128/AEM.02580-10
27. Samuel D, Estroumza J, Ailhaud G (1970) Partial purification and properties of acyl-CoA synthetase of Escherichia coli. Eur J Biochem 12(3):576–582
28. Scheps D, Honda Malca S, Richter SM, Marisch K, Nestl BM, Hauer B (2013) Synthesis of omega-hydroxy dodecanoic acid based on an engineered CYP153A fusion construct. Microb Biotechnol 6(6):694–707. doi:10.1111/1751-7915.12073
29. Schmelter T, Trigatti BL, Gerber GE, Mangroo D (2004) Biochemical demonstration of the involvement of fatty acyl-CoA synthetase in fatty acid translocation across the plasma membrane. J Biol Chem 279(23):24163–24170. doi:10.1074/jbc.M313632200
30. Schneider S, Wubbolts MG, Sanglard D, Witholt B (1998) Biocatalyst engineering by assembly of fatty acid transport and oxidation activities for in vivo application of cytochrome P-450BM-3 monooxygenase. Appl Environ Microbiol 64(10):3784–3790
31. Simard JR, Pillai BK, Hamilton JA (2008) Fatty acid flip-flop in a model membrane is faster than desorption into the aqueous phase. Biochemistry 47(35):9081–9089. doi:10.1021/bi800697q
32. Steen EJ, Kang Y, Bokinsky G, Hu Z, Schirmer A, McClure A, Del Cardayre SB, Keasling JD (2010) Microbial production of fatty-acid-derived fuels and chemicals from plant biomass. Nature 463(7280):559–562. doi:10.1038/nature08721
33. Trzaskowski J, Quinzler D, Bahrle C, Mecking S (2011) Aliphatic long-chain C(20) polyesters from olefin metathesis. Macromol Rapid Commun 32(17):1352–1356. doi:10.1002/marc.201100319
34. van Aalten DMF, DiRusso CC, Knudsen J, Wierenga RK (2000) Crystal structure of FadR, a fatty acid-responsive transcription factor with a novel acyl coenzyme A-binding fold. EMBO J 19(19):5167–5177
35. van den Berg B (2010) Going forward laterally: transmembrane passage of hydrophobic molecules through protein channel walls. ChemBioChem 11(10):1339–1343. doi:10.1002/cbic.201000105
36. Virk AP, Sharma P, Capalash N (2012) Use of laccase in pulp and paper industry. Biotechnol Prog 28(1):21–32. doi:10.1002/btpr.727
37. Wang X, Li L, Zheng Y, Zou H, Cao Y, Liu H, Liu W, Xian M (2012) Biosynthesis of long chain hydroxy fatty acids from glucose by engineered Escherichia coli. Bioresour Technol 114:561–566. doi:10.1016/j.biortech.2012.02.119
38. Weimar JD, DiRusso CC, Delio R, Black PN (2002) Functional role of fatty acyl-coenzyme A synthetase in the transmembrane movement and activation of exogenous long-chain fatty acids. Amino acid residues within the ATP/AMP signature motif of Escherichia coli FadD are required for enzyme activity and fatty acid transport. J Biol Chem 277(33):29369–29376. doi:10.1074/jbc.M107022200
39. Whitehouse CJ, Bell SG, Wong LL (2012) P450(BM3) (CYP102A1): Connecting the dots. Chem Soc Rev 41(3):1218–1260. doi:10.1039/c1cs15192d