Abstract
Analysis by a combination of absorption-, fluorescence-, circular dichroism-, mass- and nuclear magnetic resonance- spectrometry is often used to investigate the structure of chlorophylls. Here, we show several examples of spectroscopic determination of molecular structure of the recently-discovered chlorophylls and compare them with the well-known chlorophylls, chlorophyll a and bacteriochlorophyll a.
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References
Abraham RJ and Rowan AE (1991) Nuclear magnetic resonance spectroscopy of chlorophyll. In: Scheer H (ed) Chlorophylls, pp 797–834. CRC Press, Boca Raton
Akiyama M, Miyashita H, Watanabe T, Kise H, Miyachi S and Kobayashi M (2001) Detection of chlorophylld' and pheophytin a in a chlorophyll d-dominating oxygenic photosynthetic prokaryote Acaryochloris marina. Anal Sci 17: 205–208
Boardman NK and Thorne SW (1971) Sensitive fluorescence method for the determination of chlorophyll a/chlorophyll b rations. Biochim Biophys Acta 253: 222–231
Boxer SG, Closs GL and Katz JJ (1974) The effect of magnesium coordination on the 13C and 15N magnetic resonance spectra of chlorophyll a. The relative energies of nitrogen nπ* states as deduced from a complete assignment of chemical shifts. J Am Chem Soc 96: 7058–7066
Connolly JS, Samuel EB and Janzen AF (1982) Effects of solvent on the fluorescence properties of bacteriochlorophyll a. Photochem Photobiol 36: 565–574
Evans TA and Katz JJ (1975) Evidence for 5- and 6-coordinated magnesium in bacteriochlorophyll a from visible absorption spectroscopy. Biochim Biophys Acta 396: 414–426
French CS (1960) The chlorophylls in vivo and in vitro. In: Ruhland W (ed) Handbuch der Pflanzenphysiologie, Bd 5/1, pp 252–297, Springer-Verlag, Berlin
French CS, Smith JHC, Virgin HI and Airth RL (1956) Fluorescence spectrum curves of chlorophylls, pheophytins, phycoerythrins, phycocyanins and hypericin. Plant Physiol 31: 360–374
Geskes C, Hartwich G, Scheer H, Mantele W and Heinze J (1995) An electrochemical and spectroelectrochemical investigation of metal-substituted bacteriochlorophyll a. J Am Chem Soc 117: 7776–7783
Gloe A, Pfennig N, Brockmann H Jr and Trowitzsch W (1975) A new bacteriochlorophyll from brown-colored Chlorobiaceae. Arch Microbiol 102: 103–109
Goedheer JC (1966) Visible absorption and fluorescence of chlorophyll and its aggregates in solution. In: Vernon LP and Seely CR (eds) The Chlorophylls, pp 147–185. Academic Press, New York
Hall DO and Rao KK (1995) Photosynthesis, 5th edition, Cambridge University Press
Hartwich G, Fiedor L, Simonin I, Cmiel E, Schäfer W, Noy D, Scherz A and Scheer H (1998) Metal-substituted bacteriochlorophylls. 1. Preparation and influence on metal and coordination on spectra. J Am Chem Soc 120: 3675–3683
Hoffmann E and Stroobant V (2002) Mass Spectrometry: Principles and Applications, Second Edition. John Wiley & Sons, Chichester
Hunt JE and Michalski TJ (1991) Desorption-ionization mass spectrometry of chlorophylls. In: Scheer H (ed) Chlorophylls, pp 835–853. CRC Press, Boca Raton
Jeffrey SW (1969) Properties of two spectrally different components in chlorophyll c preparations. Biochim Biophys Acta 177: 456–467
Jeffrey SW (1972) Preparation and some properties of crystalline chlorophyll c1 and c2 from marine algae. Biochim Biophys Acta 279: 15–33
Jeffrey SW, Mantoura RFC and Wright SW (1997) Phytoplankton Pigments in Oceanography. UNESCO, Paris
Jensen A, Aasmundrud O and Eimhjellen KE (1964) Chlorophylls of photosynthetic bacteria. Biochim Biophys Acta 88: 466–479
Karukstis KK (1991) Chlorophyll fluorescence as a physiological probe of the photosynthetic apparatus. In: Scheer H (ed) Chlorophylls, pp 769–795. CRC Press, Boca Raton
Ke B (2001) Photosynthesis. Photobiochemistry and Photobiophysics. Kluwer Academic Publishers, Dordrecht
Kishimoto N, Fukaya F, Inagaki K, Sugio T, Tanaka H and Tano T (1995) Distribution of bacteriochlorophyll a among aerobic and acidophilic bacteria and light-enhanced CO2-incorporation in Acidiphilium rubrum. FEMS Microbiol Ecol 16: 291–296
Kobayashi M (1989) Study on the molecular mechanism of photosynthetic reaction centers. Thesis, University of Tokyo
Kobayashi M (1996) Study of precise pigment composition of photosystem I-type reaction centers by means of normal-phase HPLC. J Plant Res 109: 223–230
Kobayashi M, Watanabe T, Struck A and Scheer H (1988) Mesochlorination of chlorophyll a in the course of pigment extraction FEBS Lett. 235: 293–297
Kobayashi M, Van de Meent EJ, Amesz J, Ikegami I and Watanabe T (1991) Bacteriochlorophyll g epimer as a possible reaction center component of heliobacteria. Biochim Biophys Acta 1057: 89–96
Kobayashi M, Akiyama M, Kise H, Takaichi S, Watanabe T, Shimada K, Iwaki M, Itoh S, Ishida N, Koizumi M, Kano H, Wakao N and Hiraishi A (1998a) Structural determination of the novel Zn-containing bacteriochlorophyll in Acidiphilium rubrum. Photomed Photobiol 20: 75–80
Kobayashi M, Akiyama M, Yamamura M, Kise H, Ishida N, Koizumi M, Kano H and Watanabe T (1998b) Acidiphilium rubrum and zinc-bacteriochlorophyll, part 2: Physicochemical comparison of zinc-type chlorophylls and other metallochlorophylls. In: Garab G (ed) Photosynthesis: Mechanism and Effects, Vol 2, pp 735–738. Kluwer Academic Publishers, Dordrecht
Kobayashi M, Akiyama M, Watanabe T and Kano H (1999a) Exotic chlorophylls as key components of photosynthesis. Curr Topics Plant Biol 1: 17–35
Kobayashi M, Akiyama M, Yamamura M, Kise H, Wakao N, Ishida N, Koizumi M, Kano H and Watanabe T (1999b) Comparison of physicochemical properties of metallobacteriochlorophylls and metallochlorophylls. Z Phys Chem 213: 207–214
Kobayashi M, Oh-oka H, Akutsu S, Akiyama M, Tominaga K, Kise H, Nishida F, Watanabe T, Amesz J, Koizumi M, Ishida N and Kano H (2000) The primary electron acceptor of green sulfur bacteria, bacteriochlorophyll 663, is chlorophyll a esterified with 2,6-phytadienol. Photosynth Res 63: 269–280
Latimer P, Bannister TT and Rabinowitch E (1956) Quantum yields of fluorescence of Plant Pigments. Science 124: 585–586
Lawlor DW (1993) Photosynthesis, 2nd edition. Longman Scientific & Technical, Essex
Leupold D, Struck A, Stiel H, Teuchner K, Oberländer S and Scheer H (1990) Excited-state properties of 20-chloro-chlorophyll a. Chem Phys Lett 170: 478–484
Lötjönen S and Hynninen PH (1983) Carbon-13 NMR spectra of chlorophyll a, chlorophyll á, pyrochlorophyll a and the corresponding pheophytins. Org Magn Reson 21: 757–765
Manning WM and Strain HH (1943) Chlorophyll d, a green pigment of red algae. J Biol Chem 151: 1–19
Noy D, Fiedor L, Hartwich G, Scheer H and Scherz A (1998) Metal-substituted bacteriochlorophylls. 2. Changes in redox potentials and electronic transition energies are dominated by intramolecular electrostatic interactions. J Am Chem Soc 120: 3684–3693
Noy D, Yerushalmi R, Brumfeld V, Ashur I, Scheer H, Baldridge KK and Scherz A (2000) Optical absorption and computational studies of [Ni]-bacteriochlorophyll-a. New insight into charge distribution between metal and ligands. J Am Chem Soc 122: 3937–3944
Oelze J (1985) Analysis of bacteriochlorophylls. Meth Microbiol 18: 257–284
Permentier HP, Schmidt KA, Kobayashi M, Akiyama M, Hager-Braun C, Neerken S, Miller M and Amesz J (2000) Composition and optical properties of reaction center core complexes from the green sulfur bacteria Prosthecochloris aestuarii and Chlorobium tepidum. Photosynth Res 64: 27–39
Porra RJ and Scheer H (2000) 18O and mass spectrometry in chlorophyll research: Derivation and loss of oxygen atoms at the periphery of the chlorophyll macrocycle during biosynthesis, degradation and adaptation. Photosynth Res 66: 159–175
Scheer H and Katz JJ (1975) Nuclear magnetic resonance spectroscopy of porphyrins and metalloporphyrins. In: Smith KM (ed) Porphyrins and Metalloporphyrins, pp 399–524, Elsevier, Amsterdam
Smith JHC and Benitez A (1955) Chlorophylls: Analysis in plant materials. In: Paech K and Tracey MV (eds) Moderne Methoden der P. anzenanalyse, Vol IV, pp 142–196. Springer- Verlag, Berlin
Smith KM (1975) Mass spectrometry of porphyrins and metalloporphyrins. In: Smith KM (ed) Porphyrins and Metalloporphyrins, pp 381–398, Elsevier, Amsterdam
Stanier RY and Smith JHC (1960) The chlorophylls of green bacteria. Biochim Biophys Acta 41: 478–484
Takahashi K, Itoh Y, Akiyama M, Watanabe T, Inoue K, Oba T, Umetsu M and Kobayashi M (2005) Delicate distinction between absorption spectra of bacteriochlorophyll epimers. In: van der Est A and Bruce D (eds) Photosynthesis: Fundamental Aspects to Global Perspectives, pp 46–48. Alliance Communications Group, Lawrence
Teuchner K, Stiel H, Leupold D, Scherz A, Noy D, Simonin I, Hartwich, G and Scheer H (1997) Fluorescence and excited state absorption in modified pigments of bacterial photosynthesis: A comparative study of metal-substituted bacteriochlorophylls a. J Lumin 72–74: 612–614
Treibs A (1932) Handbuch der P. anzenanalyse. Bd. III/2, pp 1351. Julius Springer, Wien
Van de Meent EJ, Kobayashi M, Erkelens C, Van Veelen PA, Otte SCM, Inoue K, Watanabe T and Amesz J (1992) The nature of the primary electron acceptor in green sulfur bacteria. Biochim Biophys Acta 1102: 371–378
Wakao N, Shiba T, Hiraishi A, Ito M and Sakurai Y (1993) Distribution of bacteriochlorophyll a in species of the genus Acidiphilium. Curr Microbiol 27: 277–279
Watanabe T and Kobayashi M (1988) Chlorophylls as functional molecules in photosynthesis: molecular composition in vivo and physical chemistry in vitro. Nippon Kagaku Kaishi 4: 383–395
Watanabe T and Kobayashi M (1991) Electrochemistry of chlorophylls. In: Scheer H (ed) Chlorophylls, pp 287–315. CRC Press, Boca Raton
Watanabe T, Hongu A, Honda K, Nakazato M, Konno M and Saitoh S (1984) Preparation of chlorophylls and pheophytins by isocratic liquid chromatography. Anal Chem 56: 251–256
Watanabe T, Machida K, Suzuki H, Kobayashi M and Honda K (1985) Photoelectrochemistry of chlorophylls. Coord Chem Rev 64: 207–224
Weber G and Teale FWJ (1957) Determination of the absolute quantum yield of fluorescent solutions. Trans Faraday Soc 53: 646–655
Weiss C (1978) Electronic Absorption Spectra of Chlorophylls. In: Dolphin D (ed) The Porphyrins, Vol. III, Physical Chemistry, Part A, pp 211–223. Academic Press, New York
White RC, Jones ID, Gibbs E and Butler LS (1972) Fluorometric estimation of chlorophylls, chlorophyllides, pheophytins and pheophorbides in mixtures. J Agric Food Chem 20: 773–778
Wilhelm C (1987) Purification and identification of chlorophyll c1 from the green alga Mantoniella squamata. Biochim Biophys Acta 892: 23–29
Wolf H and Scheer H (1973) Stereochemistry and chiroptic properties of pheophorbides and related compounds. Ann NY Acad Sci 206: 549–567
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Kobayashi, M., Akiyama, M., Kano, H., Kise, H. (2006). Spectroscopy and Structure Determination. In: Grimm, B., Porra, R.J., Rüdiger, W., Scheer, H. (eds) Chlorophylls and Bacteriochlorophylls. Advances in Photosynthesis and Respiration, vol 25. Springer, Dordrecht. https://doi.org/10.1007/1-4020-4516-6_6
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DOI: https://doi.org/10.1007/1-4020-4516-6_6
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