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Genetic Manipulation of Quinone Biosynthesis in Cyanobacteria

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Photosystem I

Part of the book series: Advances in Photosynthesis and Respiration ((AIPH,volume 24))

Abstract

Isoprenoid quinones (phylloquinone, plastoquinone) and their derivatives (α-, β-, and γ-tocopherol) play crucial roles in oxygenic photosynthesis. Phylloquinone (vitamin K1) and plastoquinone-9 are cofactors of Photosystem I (PS I) and Photosystem II (PS II) complexes, respectively, and mediate electron transfer within and between complexes, while the roles of tocopherols are yet to be fully identified. Traditionally, the biosynthetic pathways of these quinones have been studied by direct enzymatic assays or, since the late 1960s, by using isotopic tracer compounds. Recent progress in the genome sequencing of 14 cyanobacteria has provided a newtool for the identification of genes encoding enzymes of the biosynthetic pathways of these quinones; comparative genomics, in combination with reverse genetics, has recently provided a wealth of new information. With the exception of Gloeobacter violaceus, phylloquinone biosynthesis in cyanobacteria has been shown to be very similar to menaquinone biosynthesis in Escherichia coli. Metabolic engineering of the pathway resulted in the incorporation of a variety of quinone species of either biotic or abiotic origin into the A1 site of Photosystem I, and the resulting strains are important tools for the investigation of electron transfer around the A1 quinone. Plastoquinone-9 biosynthesis in cyanobacteria differs from that in higher plants. Comparative genome analysis has revealed the presence of conserved open reading frames, which encode proteins that share sequence similarity with those required for ubiquinone biosynthesis in E. coli. Possible applications of metabolic engineering of the plastoquinone-9 and α-tocopherol biosynthetic pathways for studies of oxygenic photosynthesis are also discussed.

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References

  • Alfonso M, Perewoska I and Kirilovsky D (2000) Redox control of psbA gene expression in the cyanobacterium Synechocystis PCC 6803. Involvement of the cytochrome b6/f complex. Plant Physiol 122: 505–516

    Article  PubMed  CAS  Google Scholar 

  • Allen JF and Pfannschmidt T (2000) Balancing the two photosystems: photosynthetic electron transfer governs transcription of reaction centre genes in chloroplasts. Phil Trans R Soc Lond B Biol Sci 355: 1351–1359

    Article  CAS  Google Scholar 

  • Allen CF, Franke H and Hirayama O (1967) Identification of plastoquinone and two naphthoquinones in Anacystis nidulans by NMR and mass spectroscopy. Biochem Biophys Res Commun 26: 562–568

    Article  PubMed  CAS  Google Scholar 

  • Azzi A, Ricciarelli R and Zingg JM (2002) Non-antioxidant molecular functions of α-tocopherol (vitamin E). FEBS Lett 519: 8–10

    Article  PubMed  CAS  Google Scholar 

  • Barber J and Anderson JM (2002) Introduction. Phil Trans R Soc Lond B 357: 1325–1328

    Article  Google Scholar 

  • Ben-Shem A, Frolow F and Nelson N (2003) Crystal structure of plant photosystem I. Nature 426: 630–635

    Article  PubMed  CAS  Google Scholar 

  • Ben-Shem A, Frolow F and Nelson N (2004) Evolution of photosystem I –from symmetry through pseudosymmetry to asymmetry. FEBS Lett 564: 274–280

    Article  PubMed  CAS  Google Scholar 

  • Biggins J (1990) Evaluation of selected benzoquinones, naphthoquinones, and anthraquinones as replacements for phylloquinone in the A1 acceptor site of the Photosystem I reaction center. Biochemistry 29: 7259–7264

    Article  PubMed  CAS  Google Scholar 

  • Biggins J and Mathis P (1988) Functional role of vitamin K1 in Photosystem I of the cyanobacterium Synechocystis 6803. Biochemistry 27: 1494–1500

    Article  PubMed  CAS  Google Scholar 

  • Brettel K (1997) Electron transfer and arrangement of the redox cofactors in photosystem I. Biochim Biophys Acta 1318: 322–373

    Article  CAS  Google Scholar 

  • Brettel K and Leibl W (2001) Electron transfer in Photosystem I. Biochim Biophys Acta 1507: 100–114

    Article  PubMed  CAS  Google Scholar 

  • Brettel K, Sétif P and Mathis P (1987) Flash-induced absorption changes in Photosystem I at low temperature: evidence that the electron acceptor A1 is vitamin K1. FEBS Lett 203: 220–224

    Article  Google Scholar 

  • Bryant DA (1994) The Molecular Biology of Cyanobacteria. Kluwer Academic Publisher, Dordrecht

    Google Scholar 

  • Bryant DA (2003) The beauty in small things revealed. Proc Natl Acad Sci USA 17: 9647–9649

    Article  CAS  Google Scholar 

  • Cheng Z, Sattler S, Maeda H, Sakuragi Y, Bryant DA and DellaPenna D (2003) Highly divergent methyltransferase catalyzes a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic prokaryotes. Plant Cell 15: 2343–2356

    Article  PubMed  CAS  Google Scholar 

  • Collakova E and DellaPenna D (2001) Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis. Plant Physiol 127: 1–12

    Article  Google Scholar 

  • Collakova E and DellaPenna D (2003) Homogentisate phytyltransferase activity is limiting for tocopherol biosynthesis in Arabidopsis. Plant Physiol 131: 632–642

    Article  PubMed  CAS  Google Scholar 

  • Collins MD and Jones D (1981) Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implications. Microbiol Rev 45: 316–354

    PubMed  CAS  Google Scholar 

  • Dähnhardt D, Falk J, Appel J, van der Kooij TAW, Schulz-Friedrich R and Krupinska K (2002) The hydroxyphenylpyruvate dioxygenase from Synechocystis sp. PCC 6803 is not required for plastoquinone biosynthesis. FEBS Lett 523: 177–181

    Article  PubMed  Google Scholar 

  • Deisenhofer J and Norris JR (1993) The Photosynthetic Reaction Center, Vol 1. Academic Press, San Diego

    Google Scholar 

  • Delwiche FC and Palmer JD (1997) The origin of plastids and their spread via secondary endosymbiosis. In: Bhattacharya D (ed) Origins of Algae and Their Plastids, pp 53–86. Springer-Verlag, New York

    Google Scholar 

  • d’Harlingue A and Camara B (1985) Plastid enzymes of terpenoid biosynthesis. J Biol Chem 260: 15200–15203

    PubMed  CAS  Google Scholar 

  • Douglas SD (1998) Plastid evolution: origins, diversity, trends. Curr Opin Genet Dev 8: 655–661

    Article  PubMed  CAS  Google Scholar 

  • Dufresne A, Salanoubat M, Partensky F, Artiguenave F, Axmann IM, Barbe V, Duprat S, Galperin MY, Koonin EV, Le Gall F, Makarova KS, Ostrowski M, Oztas S, Robert C, Rogozin IB, Scanlan DJ, Tandeau de Marsac N, Weissenbach J, Wincker P, Wolf YI and Hess WR (2003) Genome sequence of the cyanobacterium Prochlorococcus marinus SS120, a nearly minimal oxyphototrophic genome. Proc Natl Acad Sci USA 100: 9647–9649

    Article  CAS  Google Scholar 

  • Durán RV, Hervás M, de la Rosa MA and Navarro JA (2004) The efficient functioning of photosynthesis and respiration in Synechocystis sp. PCC 6803 strictly requires the presence of either cytochrome c6 or plastocyanin. J Biol Chem 279: 7229–7233

    Article  PubMed  CAS  Google Scholar 

  • Escoubas JM, Lomas M, LaRoche J and Falkowski PG (1995) Light intensity regulation of cab gene transcription is signaled by the redox state of the plastoquinone pool. Proc Natl Acad Sci USA 92: 10237–10241

    Article  PubMed  CAS  Google Scholar 

  • Evans HM and Bishop BKS (1922) Fetal resorption. Science 55: 650

    Article  Google Scholar 

  • Falkowski PG (2002) The ocean’s invisible forest. Sci Am 287: 54–61

    Article  PubMed  Google Scholar 

  • Fromme P, Jordan P and Krauß N (2001) Structure of photosystem I. Biochim Biophys Acta 1507: 5–31

    Article  PubMed  CAS  Google Scholar 

  • Fromme P, Melkozernov A, Jordan P and Krauß N (2003) Structure and function of photosystem I: interactions with its soluble electron carriers and external antenna systems. FEBS Lett 555: 40–44

    Article  PubMed  CAS  Google Scholar 

  • Glockner G, Rosenthal A and Valentin K (2000) The structure and gene repertoire of an ancient red algal plastid genome. J Mol Evol 51: 382–390

    PubMed  CAS  Google Scholar 

  • Golbeck JH (1994) Photosystem I in cyanobacteria. In: Bryant DA (ed) The Molecular Biology of Cyanobacteria, pp 319–360. Kluwer Academic Publishers, Dordrecht

    Google Scholar 

  • Golbeck JH (1995) Photosystem I and its bacterial counterparts. In: Song PS and Horspool W (eds) CRC Handbook of Organic Photochemistry and Photobiology, pp 1407–1419. CRC Press, Boca Raton, FL

    Google Scholar 

  • Golbeck JH (1998) Comparison of in vitro and in vivo mutants of PsaC in photosystem I: protocols for mutagenesis and techniques for analysis. Methods Enzymol 297: 95–123

    CAS  Google Scholar 

  • Golbeck JH (2003) The binding of cofactors to Photosystem I analyzed by spectroscopic and mutagenic methods. Annu Rev Biophys Biomol Struct 32: 237–256

    Article  PubMed  CAS  Google Scholar 

  • Hauska G (1988) Phylloquinone in Photosystem I. Are quinones the secondary-electron acceptors in all types of photosynthetic reaction centers. Trends Biochem Sci 13: 415–416

    Article  PubMed  CAS  Google Scholar 

  • Honda D, Yokota A and Sugiyama J (1999) Detection of seven major evolutionary lineages in cyanobacteria based on the 16S rRNA gene sequence analysis with new sequences of five marine Synechococcus strains. J Mol Evol 48: 723–739

    Article  PubMed  CAS  Google Scholar 

  • Itoh S and Iwaki M (1989a) Vitamin K1 (phylloquinone) restores the turnover of FeS centers in the ether-extracted spinach PS I particles. FEBS Lett 243: 47–52

    Article  CAS  Google Scholar 

  • Itoh S and Iwaki M (1989b) New herbicide-binding site in the photosynthetic electron-transport chain. Competitive herbicide binding at the photosystem I phylloquinone-(vitamin K1)-binding site. FEBS Lett 250: 441–447

    Article  CAS  Google Scholar 

  • Itoh S and Iwaki M (1991) Full replacement of the function of the secondary electron acceptor phylloquinone (=vitamin K1) by non-quinone carbonyl compounds in green plant Photosystem I photosynthetic reaction center. Biochemistry 30: 5340–5346

    Article  PubMed  CAS  Google Scholar 

  • Itoh S, Iwaki M and Ikegami I (2001) Modification of Photosystem I reaction center by the extraction and exchange of chlorophylls and quinones. Biochim Biophys Acta 1507: 115–138

    Article  PubMed  CAS  Google Scholar 

  • Iwaki M and Itoh S (1989) Electron transfer in spinach Photosystem I reaction center containing benzo-, naphtho- and anthraquinones in place of phylloquinone. FEBS Lett 256: 11–16

    Article  CAS  Google Scholar 

  • Iwaki M and Itoh S (1991) Structure of the phylloquinone-binding (QΦ) site in green plant Photosystem I reaction centers: the affinity of quinones and quinoid compounds for QΦ site. Biochemistry 30: 5347–5352

    Article  PubMed  CAS  Google Scholar 

  • Johnson TW, Shen G, Zybailov B, Folling D, Reategui R, Beauparlant S, Vassiliev IR, Bryant DA, Jones AD, Golbeck JH and Chitnis PR (2000) Recruitment of a foreign quinone into the A1 site of Photosystem I: I. Genetic and physiological characterization of phylloquinone biosynthetic pathway mutants in Synechocystis sp. PCC 6803. J Biol Chem 275: 8523–8530

    Article  PubMed  CAS  Google Scholar 

  • Johnson TW, Zybailov B, Jones AD, Bittl R, Zech S, Stehlik D, Golbeck JH and Chitnis PR (2001) Recruitment of a foreign quinone into the A1 site of Photosystem I: in vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803. J Biol Chem 276: 39512–39521

    Article  PubMed  CAS  Google Scholar 

  • Johnson TW, Naithani S, Stewart C Jr, Zybailov B, Jones AD, Golbeck JH and Chitnis PR (2003) The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803. Biochim Biophys Acta 1557: 67–76

    Article  CAS  Google Scholar 

  • Jordan P, Fromme P, Witt HT, Klukas O, Saenger W and Krauß N (2001) Three-dimensional structure of cyanobacterial Photosystem I at 2.5 Å resolution. Nature 411: 896–899

    Article  Google Scholar 

  • Kamal-Eldin A and Appelqvist L-A (1996) The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31: 671–701

    Article  PubMed  CAS  Google Scholar 

  • Kaneko T, Sato S, Kotani H, Tanaka A, Asamizu E, Nakamura Y, Miyajima N, Hirosawa M, Sugiura M, Sasamoto S, Kimura T, Hosouchi T, Matsuno A, Muraki A, Nakazaki N, Naruo K, Okumura S, Shimpo S, Takeuchi C, Wada T, Watanabe A, Yamada M, Yasuda M and Tabata S (1996) Sequence analysis of the genome of the unicellular cyanobacterium Synechocystis sp. strain PCC6803. II. Sequence determination of the entire genome and assignment of potential protein-coding regions. DNA Res 3: 109–136

    Article  PubMed  CAS  Google Scholar 

  • Kaneko T, Nakamura Y, Wolk CP, Kuritz T, Sasamoto T, Watanabe A, Iriguchi M, Ishikawa M, Kawashima M, Kimura T, Kishida Y, Kohara M, Matsumoto M, Matsuno A, Muraki A, Nakazaki N, Shimpo S, Sugimoto M, Takazawa M, Yamada M, Yasuda M and Tabata S (2001) Complete genomic sequence of the filamentous nitrogen-fixing cyanobacterium Anabaena sp. strain PCC 7120. DNA Res 8: 205–213

    Article  PubMed  CAS  Google Scholar 

  • Ke B (2001) Photosynthesis: Photobiochemistry and Photobiophysics. Kluwer Academic Publishers, Dordrecht

    Google Scholar 

  • Koch M, Lemke R, Heise K and Mock H (2003) Characterization of Γ-tocopherol methyltransferase from Capsicum annuum L. and Arabidopsis thaliana. Eur J Biochem 270: 84–92

    Article  PubMed  CAS  Google Scholar 

  • Lee PT, Hsu AY, Ha HT and Clarke CF (1997) A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of Escherichia coli ubiE gene. J Bacteriol 179: 1748–1754

    PubMed  CAS  Google Scholar 

  • Li H and Sherman LA (2000) A redox-responsive regulator of photosynthesis gene expression in the cyanobacterium Synechocystis sp. Strain PCC 6803. J Bacteriol 182: 4268–4277

    Article  PubMed  CAS  Google Scholar 

  • Li N, Zhao JD, Warren PV, Warden JT, Bryant DA and Golbeck JH (1991) PsaD is required for the stable binding of PsaC to the Photosystem I core protein of Synechococcus sp. PCC 6301. Biochemistry 30: 7863–7872

    Article  PubMed  CAS  Google Scholar 

  • Margulis L (1970) Origin of Eukaryotic Cells. Yale University Press, New Haven

    Google Scholar 

  • Martin W, Stoebe B, Gremykin V, Hapsmann S, Hasegawa M and Kowallik KV (1998) Gene transfer to the nucleus and the evolution of chloroplast. Nature 393: 162–165

    Article  PubMed  CAS  Google Scholar 

  • Matsuzaki M, Misumi O, Shin-IT, Maruyama S, Takahara M, Miyagishima SY, Mori T, Nishida K, Yagisawa F, Nishida K, Yoshida Y, Nishimura Y, Nakao S, Kobayashi T, Momoyama Y, Higashiyama T, Minoda A, Sano M, Nomoto H, Oishi K, Hayashi H, Ohta F, Nishizaka S, Haga S, Miura S, Morishita T, Kabeya Y, Terasawa K, Suzuki Y, Ishii Y, Asakawa S, Takano H, Ohta N, Kuroiwa H, Tanaka K, Shimizu N, Sugano S, Sato N, Nozaki H, Ogasawara N, Kohara Y and Kuroiwa T (2004) Genome sequence of the ultrasmall unicellular red alga Cyanidioschyzon merolae 10D. Nature 428: 653–657

    Article  PubMed  CAS  Google Scholar 

  • McKenna M, Henninger MD and Crane FL (1964) A second naphthoquinone in spinach chloroplasts. Nature 203: 524–525

    Article  PubMed  CAS  Google Scholar 

  • Meganathan R (1996) Biosynthesis of the isoprenoid quinones-menaquinone (vitamin K2) and ubiquinone (coenzyme Q). In: Neidhardt FC (ed) Escherichia coli and Salmonella –Cellular and Molecular Biology, Vol 2, pp 642–656. ASM press, Washington, DC

    Google Scholar 

  • Meganathan R (2001) Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm 61: 173–218

    PubMed  CAS  Google Scholar 

  • Mehari T, Qiao F, Scott MP, Nellis DF, Zhao J, Bryant DA and Golbeck JH (1995) Modified ligands to FA and FB in Photosystem I. I. Structural constraints for the formation of iron–sulfur clusters in free and rebound PsaC. J Biol Chem 270: 28108–29117

    Article  PubMed  CAS  Google Scholar 

  • Monzingo AF, Gao J, Qiu J, Georgiou G and Robertus JD (2003) The X-ray structure of Escherichia coli RraA (MenG), a protein inhibitor of RNA processing. J Mol Biol 332: 1015–1024

    Article  PubMed  CAS  Google Scholar 

  • Mühlenhoff U, Kruip J, Nitschke W, Bryant DA, Rögner M, Sétif P and Boekema E (1996a) Characterization of a redox active cross-linking complex between cyanobacterial photosystem I and its physiological acceptor flavodoxin. EMBO J 15: 488–497

    Google Scholar 

  • Mühlenhoff U, Zhao J and Bryant DA (1996b) Interaction of Photosystem I and flavodoxin from the cyanobacterium Synechococcus sp. PCC 7002 as revealed by chemical cross-linking. Eur J Biochem 325: 324–331

    Article  Google Scholar 

  • Nakamura Y, Kaneko T, Sato S, Ikeuchi M, Katoh H, Sasamoto S, Watanabe A, Iriguchi M, Kawashima K, Kimura T, Kishida Y, Kiyokawa C, Kohara M, Matsumoto M, Matsuno A, Nakazaki N, Shinpo S, Sugimoto M, Takeuchi C, Yamada M and Tabata S (2002) Complete genome structure of the thermophilic cyanobacterium Thermosynechococcus elongatus BP-1. DNA Res 9: 123–130

    Article  PubMed  CAS  Google Scholar 

  • Nakamura Y, Kaneko T, Sato S, Mimuro M, Miyashita H, Tsuchiya T, Sasamoto S, Watanabe A, Kawashima K, Kishida Y, Kiyokawa C, Kohara M, Matsumoto M, Matsuno A, Nakazaki N, Shimpo S, Takeuchi C, Yamada M and Tabata S (2003) Complete genome structure of Gloeobacter violaceus PCC 7421, a cyanobacterium that lacks thylakoids. DNA Res 10: 137–145

    Article  PubMed  CAS  Google Scholar 

  • Nelissen B, Van de Peer Y, Wilmotte A and De Wachter R (1995) An early origin of plastids within the cyanobacterial divergence is suggested by evolutionary trees based on complete 16S rRNA sequences. Mol Biol Evol 12: 1166–1173

    PubMed  CAS  Google Scholar 

  • Norris SR, Shen X and DellaPenna D (1998) Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase. Plant Physiol 117: 1317–1323

    Article  PubMed  CAS  Google Scholar 

  • Ohta N, Matsuzaki M, Misumi O, Miyagishima SY, Nozaki H, Tanaka K, Shin-IT, Kohara Y and Kuroiwa T (2003) Complete sequence and analysis of the plastid genome of the unicellular red alga Cyanidioschyzon merolae. DNA Res 10: 67–77

    Article  PubMed  CAS  Google Scholar 

  • Ort DR and Yocum CF (1996) Oxygenic Photosynthesis: The Light Reactions. Kluwer Academic Publishers, Dordrecht

    Google Scholar 

  • Palenik B, Brahamsha B, Larimer FW, Land M, Hauser L, Chain P, Lamerdin J, Regala W, Allen EE, McCarren J, Paulsen I, Dufresne A, Partensky F, Webb EA and Waterbury J (2003) The genome of a motile marine Synechococcus. Nature 424: 1037–1042

    Article  PubMed  CAS  Google Scholar 

  • Pennock JF and Threlfall DR (1981) Biosynthesis of ubiquinone and related compounds. In: Porter JW and Spurgeon SL (eds) Biosynthesis of Isoprenoid Compounds, Vol 2, pp 191–303. John Wiley & Sons, New York

    Google Scholar 

  • Petersen J, Stehlik D, Gast P and Thurnauer M (1987) Comparison of the electron spin polarized spectrum found in plant Photosystem I and in iron-depleted bacterial reaction centers with time-resolved K-band EPR; evidence that the Photosystem I acceptor A1 is a quinone. Photosynth Res 14: 15–29

    Article  CAS  Google Scholar 

  • Porfirova S, Bergmuller E, Tropf S, Lemke R and Dormann P (2002) Isolation of an Arabidopsis mutant lacking vitamin E and identification of a cyclase essential for all tocopherol biosynthesis. Proc Natl Acad Sci USA 99: 12495–12500

    Article  PubMed  CAS  Google Scholar 

  • Prince RC, Gunner MR and Dutton PL (1982) Quinones of value to electron-transfer studies: oxidation–reduction potentials of the first reduction step in an aprotic solvent. In: Trumpower BL (ed) Function of Quinones in Energy Conserving Systems, pp 29–33. Academic Press, New York

    Google Scholar 

  • Prince RC, Dutton PL and Bruce JM (1983) Electrochemistry of ubiquinones: menaquinones and plastoquinones in aprotic solvents. FEBS Lett 160: 273–276

    Article  CAS  Google Scholar 

  • Prince RC, Lloyd-Williams P, Bruce JM and Dutton PL (1986) Voltammetric measurements of quinones. Methods Enzymol 125: 109–119

    PubMed  CAS  Google Scholar 

  • Ricciarelli R, Zingg J-M and Azzi A (2002) The 80th anniversary of vitamin E: beyond its antioxidant properties. Biol Chem 383: 457–465

    Article  PubMed  CAS  Google Scholar 

  • Rocap G, Larimer FW, Lamerdin J, Malfatti S, Chain P, Ahlgren NA, Arellano A, Coleman M, Hauser L, Hess WR, Johnson ZI, Land M, Lindell D, Post AF, Regala W, Shah M, Shaw SL, Steglich C, Sullivan MB, Ting CS, Tolonen A, Webb EA, Zinser ER and Chisholm SW (2003) Genome divergence in two Prochlorococcus ecotypes reflects oceanic niche differentiation. Nature 424: 1042–1047

    Article  PubMed  CAS  Google Scholar 

  • Sakuragi Y (2004) Cyanobacterial quinomics –studies of quinones in cyanobacteria. PhD Thesis. The Pennsylvania State University

    Google Scholar 

  • Sakuragi Y, Zybailov B, Shen G, Jones AD, Chitnis PR, van der Est A, Bittl R, Zech S, Stehlik D, Golbeck JH and Bryant DA (2002) Insertional inactivation of the menG gene, encoding 2-phytyl-1,4-naphthoquinone methyltransferase of Synechocystis sp. PCC 6803, results in the incorporation of 2-phytyl-1,4-naphthoquinone into the A1 site and alteration of the equilibrium constant between A1 and FX in Photosystem I. Biochemistry 41: 394–405

    Article  PubMed  CAS  Google Scholar 

  • Sakuragi Y, Zybailov B, Shen G, Bryant DA, Golbeck, JH, Diner BA, Karygina I, Pushkar Y and Stehlik D (2005) Recruitment of a foreign quinone into the A1 site of photosystem I. Characterization of a menB rubA double deletion mutant in Synechococcus sp. PCC 7002 devoid of FX, FA, and FB and containing plastoquinone or exchanged 9,10-anthraquinone. J Biol Chem 280: 12371–12381

    Article  PubMed  CAS  Google Scholar 

  • Sattler S, Cahoon EB, Coughlan SJ and DellaPenna D (2003) Characterization of tocopherol cyclases from higher plants and cyanobacteria. Evolutionary implications for tocopherol synthesis and function. Plant Phys 132: 2184–2195

    Article  CAS  Google Scholar 

  • Sattler S, Gillilanda LU, Magallanes-Lundback M, Pollard M and DellaPenna D (2004) Vitamin E is essential for seed longevity and preventing lipid peroxidation during germination. Plant Cell 16: 1419–1432

    Article  PubMed  CAS  Google Scholar 

  • Savidge B, Weiss JD, Wong YH, Lassner NW, Mitsky TA, Shewmaker CK, Post-Beittenmiller D and Valentin HE (2002) Isolation and characterization of homogentisate phytyltransferase genes from Synechocystis sp. PCC 6803 and Arabidopsis. Plant Physiol 129: 321–332

    Article  PubMed  CAS  Google Scholar 

  • Schledz M, Seidler A, Beyer P and Neuhaus G (2001) A novel phytyltransferase from Synechocystis sp. PCC 6803 involved in tocopherol biosynthesis. FEBS Lett 499: 15–3589

    Article  PubMed  CAS  Google Scholar 

  • Schoeder H-U and Lockau W (1986) Phylloquinone copurified with the large subunits of Photosystem I. FEBS Lett 199: 23–27

    Article  CAS  Google Scholar 

  • Schopf JW (1993) Microfossils of the early archean apex chert: new evidence of the antiquity of life. Science 260: 640–646

    Article  PubMed  CAS  Google Scholar 

  • Semenov AY, Vassiliev IR, van der Est A, Mamedov MD, Zybailov B, Shen G, Stehlik D, Diner BA, Chitnis PR and Golbeck JH (2000) Recruitment of a foreign quinone into the A1 site of Photosystem I: altered kinetics of electron transfer in phylloquinone biosynthetic pathway mutants studied by time-resolved optical, EPR, and electromagnetic techniques. J Biol Chem 275: 23429–23438

    Article  PubMed  CAS  Google Scholar 

  • Sétif P (2001) Ferredoxin and flavodoxin reduction by photosystem I. Biochim Biophys Acta 1507: 161–179

    Article  PubMed  Google Scholar 

  • Shen G, Zhao J, Reimer SK, Antonkine ML, Cai Q, Weiland SM, Golbeck JH and Bryant DA (2002a) Assembly of Photosystem I: I. Inactivation of the rubA gene encoding a membrane-associated rubredoxin in the cyanobacterium Synechococcus sp. PCC 7002 causes a loss of Photosystem I activity. J Biol Chem 277: 20343–20354

    Article  CAS  Google Scholar 

  • Shen G, Antonkine ML, van der Est A, Vassiliev IR, Brettel K, Bittl R, Zech SG, Zhao J, Stehlik D, Bryant DA and Golbeck JH (2002b) Assembly of Photosystem I. II. Rubredoxin is required for the in vivo assembly of FX in Synechococcus sp. PCC 7002 as shown by optical and EPR spectroscopy. J Biol Chem 277: 20355–20366

    Article  CAS  Google Scholar 

  • Shinkarev VP, Zybailov B, Vassiliev IR and Golbeck JH (2002) Modeling of the P700+ charge recombination kinetics with phylloquinone and plastoquinone in the A1 site of Photosystem I. Biophys J 83: 2885–2897

    Article  PubMed  CAS  Google Scholar 

  • Shintani D and DellaPenna D (1998) Elevating the vitamin E content of plants through metabolic engineering. Science 282: 2098–2100

    Article  PubMed  CAS  Google Scholar 

  • Shintani D, Cheng Z and DellaPenna D (2002) The role of 2-methyl-6-phytyl-benzoquinone methyltransferase in determining tocopherol composition in Synechocystis sp. PCC 6803. FEBS Lett 511: 1–5

    Article  PubMed  CAS  Google Scholar 

  • Simantiras M and Leistner E (1991) Cell free synthesis of ortho-succinylbenzoic acid in protein extracts from anthraquinone and phylloquinone (vitamin K1) producing plant-cell suspensions cultures –occurrence of intermediates between isochorismic and ortho-succinylbenzoic acid. Z Naturforsch C 46: 364–370

    CAS  Google Scholar 

  • Soll J, Kemmerling M and Schultz G (1980) Tocopherol and plastoquinone synthesis in spinach chloroplasts subfractions. Arch Biochem Biophys 204: 544–550

    Article  PubMed  CAS  Google Scholar 

  • Soll J, Schultz G, Joyard J, Douce R and Block MA (1985) Localization and synthesis of prenylquinones in isolated outer and inner envelope membranes from spinach chloroplast. Arch Biochem Biophys 238: 290–299

    Article  PubMed  CAS  Google Scholar 

  • Swiezewska E (2004) Ubiquinone and plastoquinone metabolism in plants. Methods Enzymol 378: 124–131

    Article  PubMed  CAS  Google Scholar 

  • Takahashi Y, Hirota K and Katoh S (1985) Multiple forms of P700-chlorophyll a–protein complex from Synechococcus sp.: the iron, quinone and carotenoid contents. Photosynth Res 6: 183–192

    Article  CAS  Google Scholar 

  • Thornber JP, Alberte RS, Hunter FA, Shiozawa JA and Kan K-S (1976) The organization of chlorophyll in the plant photosynthetic unit. Brookhaven Symp Biol 28: 132–148

    PubMed  Google Scholar 

  • Threlfall DR and Whistance GR (1971) Biosynthesis of isoprenoid quinones and chromanols. In: Goodwin TW (ed) Aspects of Terpenoid Chemistry and Biochemistry, Vol 12, pp 357–404. Academic Press, New York

    Google Scholar 

  • Trebst A, Depka BM and Hollander-Czytko H (2002) A specific role for tocopherol and of chemical singlet oxygen quenchers in the maintenance of Photosystem II structure and function in Chlamydomonas reinhardtii. FEBS Lett 516: 156–160

    Article  PubMed  CAS  Google Scholar 

  • Vassiliev IR, Antonkine ML and Golbeck JH (2001) Iron–sulfur clusters in type I reaction centers. Biochim Biophys Acta 1507: 139–160

    Article  PubMed  CAS  Google Scholar 

  • Yoshida E, Nakamura A and Watanabe A (2003) Reversed-phase HPLC determination of chlorophyll a′ and naphthoquinones in Photosystem I of red algae: existence of two menaquinone-4 molecules in Photosystem I of Cyanidium caldarium. Anal Sci 19: 1001–1005

    Article  PubMed  CAS  Google Scholar 

  • Zhao JD, Warren PV, Li N, Bryant DA and Golbeck JH (1990) Reconstitution of electron transport in Photosystem I with PsaC and PsaD proteins expressed in Escherichia coli. FEBS Lett 276: 175–180

    Article  PubMed  CAS  Google Scholar 

  • Zhao J, Li N, Warren PV, Golbeck JH and Bryant DA (1992) Site-directed conversion of a cysteine to aspartate leads to the assembly of a [3Fe–4S] cluster in PsaC of Photosystem I. The photoreduction of FA is independent of FB at low temperature. Biochemistry 31: 5093–5099

    Article  PubMed  CAS  Google Scholar 

  • Zhao J, Snyder WB, Mühlenhoff U, Rhiel E, Warren PV, Golbeck JH and Bryant DA (1993) Cloning and characterization of the psaE gene of the cyanobacterium Synechococcus sp. PCC 7002: characterization of a psaE mutant and overproduction of the protein in Escherichia coli. Mol Microbiol 9: 183–194

    Article  PubMed  CAS  Google Scholar 

  • Ziegler K, Maldener I and Lockau W (1989) 5′-Monohydroxyphylloquinone as a component of Photosystem I. Z Natuforsch C 44: 468–472

    CAS  Google Scholar 

  • Zybailov B (2003) Modified quinone acceptor in photosystem I. PhD Thesis. The Pennsylvania State University

    Google Scholar 

  • Zybailov B, van der Est A, Zech SG, Teutloff C, Johnson TW, Shen G, Bittle R, Stehlik D, Chitnis PR and Golbeck JH (2000) Recruitment of a foreign quinone into the A1 site of Photosystem I: II. Structural and functional characterization of phylloquinone biosynthetic pathway mutants by electron paramagnetic resonance and electron-nuclear double resonance spectroscopy. J Biol Chem 275: 8531–8539

    Article  PubMed  CAS  Google Scholar 

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Sakuragi, Y., Bryant, D.A. (2006). Genetic Manipulation of Quinone Biosynthesis in Cyanobacteria. In: Golbeck, J.H. (eds) Photosystem I. Advances in Photosynthesis and Respiration, vol 24. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-4256-0_15

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