Biotransformation of menadione to its prenylated derivative MK-3 using recombinant Pichia pastoris

Journal of Industrial Microbiology and Biotechnology

Volumn 44, Issue 7, 2017, Pages 973-985

  Li, Zhemin ^a   Zhao, Genhai ^a   Liu, Hui ^a   Guo, Yugang ^b   Wu, Hefang ^a   Sun, Xiaowen ^a   Wu, Xihua ^a   Zheng, Zhiming ^a  

^a HEFEI INSTITUTES OF PHYSICAL SCIENCE   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Aromatic prenyltransferase; Chemoenzymatic synthesis; Menadione prenylation; Pichia pastoris; Whole cell catalysis

Indexed keywords

1,4 NAPHTHOQUINONE; CALCIUM; COBALT; COPPER; DETERGENT; DIMETHYLALLYLTRANSFERASE; EDETIC ACID; IRON; LEVULINIC ACID; MAGNESIUM; MANGANESE; MENADIONE; MENAQUINONE; METAL ION; NICKEL; NOVQ PROTEIN; PHTHALIC ACID; PYROPHOSPHATE; UNCLASSIFIED DRUG; ZINC; 3,3-DIMETHYLALLYL PYROPHOSPHATE; BACTERIAL PROTEIN; FARNOQUINONE; HEMITERPENE; NOVQ PROTEIN, STREPTOMYCES; ORGANOPHOSPHORUS COMPOUND; PENTANOL; PRENOL; RECOMBINANT PROTEIN;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; FERMENTATION OPTIMIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; KOMAGATAELLA PASTORIS; MOLECULAR WEIGHT; NONHUMAN; OXIDATION; PH; PRENYLATION; PROTEIN EXPRESSION; WESTERN BLOTTING; ENZYME SPECIFICITY; ENZYMOLOGY; METABOLIC ENGINEERING; METABOLISM; PICHIA; STREPTOMYCES; TRANSGENIC MICROORGANISM;

BACTERIAL PROTEINS; BIOTRANSFORMATION; CATALYSIS; DIMETHYLALLYLTRANSTRANSFERASE; HEMITERPENES; HYDROGEN-ION CONCENTRATION; METABOLIC ENGINEERING; MICROORGANISMS, GENETICALLY-MODIFIED; ORGANOPHOSPHORUS COMPOUNDS; PENTANOLS; PICHIA; PRENYLATION; RECOMBINANT PROTEINS; STREPTOMYCES; SUBSTRATE SPECIFICITY; VITAMIN K 2; VITAMIN K 3;

EID: 85014248337     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-017-1931-2     Document Type: Article

References (53)

1. 3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species. EFSA J 12. doi:10.2903/j.efsa.2014.3532
2. 2 takes charge. Science 336:1241–1242. doi:10.1126/science.1223812
3. Botta B, Delle Monache G, Menendez P, Boffi A (2005) Novel prenyltransferase enzymes as a tool for flavonoid prenylation. Trends Pharmacol Sci 26:606–608. doi:10.1016/j.tips.2005.09.012
4. Curvers S, Brixius P, Klauser T, Thömmes J, Weuster-Botz D, Takors R, Wandrey C (2001) Human chymotrypsinogen B production with Pichia pastoris by integrated development of fermentation and downstream processing. Part 1. Fermentation. Biotechnol Progr 17:495–502
5. Dairi T (2012) Menaquinone biosyntheses in microorganisms. Method Enzymol 515:107–122. doi:10.1016/B978-0-12-394290-6.00006-9
6. 3 by oxidation of the methylnaphthalene fraction. Russ J Appl Chem 84:988–992
7. 2 series. CN CN20071066044, 26-12-2007
8. Geleijnse JM, Cees V, Grobbee DE, Schurgers LJ, Knapen MHJ, Meer IM, Der Van, Albert H, Witteman JCM (2004) Dietary intake of menaquinone is associated with a reduced risk of coronary heart disease: the Rotterdam Study. J Nutr 134:3100–3105
9. Guo Y, Gan L, Shen G, Wu L, Hao J, Zhong Y, Rui L, Li G, Yi S, Jie S (2012) Production and characterization of recombinant 9 and 15 kDa granulysin by fed-batch fermentation in Pichia pastoris. Appl Microbiol Biot 97:7669–7677
10. Snyder CD, Rapoport H (1974) Synthesis of menaquinones. J Am Chem Soc 96:8046–8054
11. 2 isoprenologues by reversed-phase thin-layer chromatography. J Chromatogr A 45:446–452
12. Henry LK, Gutensohn M, Thomas ST, Noel JP, Dudareva N (2015) Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants. P Natl Acad Sci USA 112:10050–10055. doi:10.1073/pnas.1504798112
13. Hong F, Meinander NQ, Jönsson LJ (2013) Fermentation strategies for improved heterologous expression of laccase in Pichia pastoris. Biotechnol Bioeng 79:438–449
14. Hu X, Chu J, Zhang S, Zhuang Y, Wu X, Chen H, Lv Z, Yuan Z (2014) An alkaline pH control strategy for methionine adenosyltransferase production in Pichia pastoris fermentation. Biotechnol Bioproc E 19:900–907
15. 3 in plasma by high-performance liquid chromatography. J Chromatogr B 666:299–305
16. Ignea C, Trikka FA, Nikolaidis AK, Georgantea P, Ioannou E, Loupassaki S, Kefalas P, Kanellis AK, Roussis V, Makris AM (2015) Efficient diterpene production in yeast by engineering Erg20p into a geranylgeranyl diphosphate synthase. Metab Eng 27:65–75
17. Lange BM, Croteau R (1999) Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway Isopentenyl monophosphate kinase catalyzes the terminal enzymatic step. P Natl Acad Sci USA 96:13714–13719
18. Jahic M, Wallberg F, Bollok M, Garcia P, Enfors SO (2003) Temperature limited fed-batch technique for control of proteolysis in Pichia pastoris bioreactor cultures. Microb Cell Fact 2:1–11
19. Kong MK, Lee PC (2011) Metabolic engineering of menaquinone-8 pathway of Escherichia coli as a microbial platform for vitamin K production. Biotechnol Bioeng 108:1997–2002. doi:10.1002/bit.23142
20. Kumano T, Richard SB, Noel JP, Nishiyama M, Kuzuyama T (2008) Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities. Bioorgan Med Chem 16:8117–8126. doi:10.1016/j.bmc.2008.07.052
21. 2 biosynthesis promising drug targets? Molecules 15:1531–1553. doi:10.3390/molecules15031531
22. Kuzuyama T, Noel JP, Richard SB (2005) Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435:983–987. doi:10.1038/nature03668
23. Luo G, Ducy P, Mckee MD, Pinero GJ, Loyer E, Behringer RR, Karsenty G (1997) Spontaneous calcification of arteries and cartilage in mice lacking matrix GLA protein. Nature 386:78–81
24. Mccormick ML, Denning GM, Reszka KJ, Bilski P, Buettner GR, Rasmussen GT, Railsback MA, Britigan BE (2000) Biological effects of menadione photochemistry: effects of menadione on biological systems may not involve classical oxidant production. Biochem J 350(Pt 3):797–804
25. 2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm 61:173–218
26. Murasugi A, Tohma-Aiba Y (2003) Production of native recombinant human midkine in the yeast, Pichia pastoris. Protein Expres Purif 27:244–252
27. Nakagawa K, Hirota Y, Sawada N, Yuge N, Watanabe M, Uchino Y, Okuda N, Shimomura Y, Suhara Y, Okano T (2010) Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme. Nature 468:117–121. doi:10.1038/nature09464
28. 2) in mice: two possible routes for menaquinone-4 accumulation in cerebra of mice. J Biol Chem 283:11270–11279. doi:10.1074/jbc.M702971200
29. Ozaki T, Mishima S, Nishiyama M, Kuzuyama T (2009) NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids. J Antibiot 62:385–392. doi:10.1038/ja.2009.48
30. Pojer F, Wemakor E, Kammerer B, Chen H, Walsh CT, Li SM, Heide L (2003) CloQ, a prenyltransferase involved in clorobiocin biosynthesis. P Natl Acad Sci USA 100:2316–2321. doi:10.1073/pnas.0337708100
31. 2 derivatives and prenylalcohols. Anticancer Res 28:151–158
32. Saleh O, Haagen Y, Seeger K, Heide L (2009) Prenyl transfer to aromatic substrates in the biosynthesis of aminocoumarins, meroterpenoids and phenazines: the ABBA prenyltransferase family. Phytochemistry 70:1728–1738. doi:10.1016/j.phytochem.2009.05.009
33. Sato K (1973) A new synthesis of vitamin K via π-allyinickel intermediates. J Chem Soc Perk Trans 1:2289–2293
34. 2)-7 by Bacillus subtilis. J Biosci Bioeng 91:16–20
35. Schoepp-Cothenet B, Lieutaud C, Baymann F, Vermeglio A, Friedrich T, Kramer DM, Nitschke W (2009) Menaquinone as pool quinone in a purple bacterium. P Natl Acad Sci USA 106:8549–8554. doi:10.1073/pnas.0813173106
36. 1 and natto-derived menaquinone-7. Blood 109:3279–3283
37. Shearer MJ, Paul N (2008) Metabolism and cell biology of vitamin K. Thromb Haemostasis 100:530–547
38. Shineberg B, Young IG (1976) Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli. Biochem US 15:2754–2758
39. Sirén N, Weegar J, Dahlbacka J, Kalkkinen N, Fagervik K, Leisola M, von Weymarn N (2006) Production of recombinant HIV-1 Nef (negative factor) protein using Pichia pastoris and a low-temperature fed-batch strategy. Biotechnol Appl Bioc 44:151–158
40. Song H, Wang J, Ding S (2002) The synthesis of coenzyme Q. Chem Adhes 10:267–268
41. Suzuki M, Nakase T (1999) A phylogenetic study of ubiquinone Q-8 species of the genera Candida, Pichia, and Citeromyces based on 18S ribosomal DNA sequence divergence. J Gen Appl Microbiol 45:239–246
42. Suzuki T, Kitamura M, Amano Y, Hashizume T (2013) Efficient use of exogenous isoprenols for protein isoprenylation by MDA-MB-231 cells is regulated independently of the mevalonate pathway. J Biol Chem 288:27444–27455
43. Takayuki H (2009) Clinical implications of undercarboxylated osteocalcin. Clin Calcium 19:1815–1821
44. 2)-6 production by mutants of Flavobacterium meningosepticum. J Nutr Sci Vitaminol 32:137–145
45. 2(Menaquinone): screening of Producing Microorganisms and Production by Flavobacterium meningosepticum. J Ferment Technol 62:321–327
46. Tani Y, Taguchi H (1988) Excretion of menaquinone-4 by a mutant of Flavobacterium sp. 238-7 in a detergent-supplemented culture (microbiology & fermentation industry). Agric Biol Chem 52:449–454
47. Tani Y, Taguchi H (1989) Extracellular production of menaquinone-4 by a mutant of Flavobacterium sp. 238-7 with a detergent-supplemented culture. J Ferment Bioeng 67:102–106
48. Tso HH, Chen YJ (2010) A convenient one-flask synthesis of vitamin K. J Chem Res, Synop 3:104–105
49. 2 (menaquinone-7) by analog resistance. Biosci Biotech Bioch 65:2007–2015. doi:10.1271/bbb.65.2007
50. 2 is a mitochondrial electron carrier that rescues pink1 deficiency. Science 336:1306–1310. doi:10.1126/science.1218632
51. Winkelblech J, Fan A, Li SM (2015) Prenyltransferases as key enzymes in primary and secondary metabolism. Appl Microbiol Biot 99:7379–7397. doi:10.1007/s00253-015-6811-y
52. Li Z, Xiong F, Lin Q, d’Anjou M, Daugulis AJ, Yang DS, Hew CL (2001) Low-temperature increases the yield of biologically active herring antifreeze protein in Pichia pastoris. Protein Expres Purif 21:438–445
53. Zhong Y, Yang L, Guo Y, Fang F, Wang D, Li R, Jiang M, Kang W, Ma J, Sun J (2014) High-temperature cultivation of recombinant Pichia pastoris increases endoplasmic reticulum stress and decreases production of human interleukin-10. Microb Cell Fact 13:1–10