Abstract
A product with molecular mass of 500–550 Da was isolated from a pigmented material formed by thermolysis (185°C) of a mixture of glutamic acid, glycine, and lysine (the optimal molar ratio of 8:3:1). After purification by chromatography the spectra of absorption and luminescence as well as IR- and PMR-spectra of the isolated pigment were studied. Based on the obtained data, the pigment was identified as a structural analogue of biological flavins: isoalloxazine heterocycle with two hydroxyl groups as well as a substitute of the amino acid nature. Like natural flavins, the abiogenic pigment photosensitized in solution both anaerobic and aerobic reactions of electron transfer from donors (ascorbate, Na2-EDTA) to acceptors (redox- sensitive dyes, nicotinamide, Mo(IV) ), with the rate practically identical to that in the case of use of riboflavin. The ability of abiogenic flavin and riboflavin to photosensitize redox reactions was preserved after absorption of their molecules on particles of clay minerals (kaolinite, bentonite, celite) ; however, the absorption affected the rate of individual photochemical reactions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Rossman, M.G., Moras, D., and Olsen, K.W., Chemical and Biological Evolution of a Nucleotide-Binding Protein, Nature, 1974, vol. 250, pp. 194–199.
Heinz, B., Ried, W., and Dose, K., Thermische Erzeugung von Pteridinen und Flavinen aus Amino-sauregemischen, Angew. Chem., 1979, vol. 91, pp. 510–511.
Krasnovskii, A.A., Development of the Mode of Action of the Photocatalitic System in Organisms. The Origin of Life on the Earth, Proc. 1st Intern. Symp., Moscow,1957, Oparin, A.I., et al., Eds., London: Pergamon, 1959, pp. 606–618.
Gaffron, G., Basic Stages of Photochemical Evolu-tion, Horizons of Biochemistry, Moscow, 1964, pp. 49–73.
Kritsky, M.S., Lyudnikova, T.A., Mironov, E.V., and Neverov, K.V., The Evolutionary Aspects of Coenzyme Photobiochemistry, Matter, Energy, and Information in the Origin of Life in the Universe, Chela Flores, J. and Raulin, F., Eds., Doderecht: Kluver Academic, 1998, pp. 187–190.
Berezovskii, V.M., Khimiya vitaminov (Chemistry of Vitamins), Moscow, 1973.
Shuvalov, V.A. and Krasnovskii, A.A., Lumines-cence of Zinc-Porphyrins in Microorganisms and Plants: Phosphorescence and Delayed Fluorescence, Molekul. Biol., 1971, vol. 5, pp. 698–710.
Bunkin, A.F., Kolesnikov, M.P., and Pershin, S.M., Laser Fluorescence of Soil: Online Re-mote Sensing of the Earth™s Surface, Physics of Vibrations, 1998, vol. 6, pp. 249–255.
Kolesnikov, M.P., Flavoproteinoids in Processes of Prebiological Evolution, Izv. RAN, Ser. Biol., 1991, pp. 325–333.
Gorbunov, N.I., Metodika podgotovki pochv k min-eralogicheskim analizam (Procedure of Preparation of Soils to Mineralogical Analyses), Moscow, 1971, pp. 5–15.
Kolesnikov, M.P. and Egorov, I.A., Abiogenic Synthesis and Catalytic Properties of Porphyrin-Pep-tide Complexes, Dokl. Akad. Nauk SSSR, 1978, vol. 241, pp. 1465–1468.
Reuter, M., Wikgren, M., and Palmberg, J., The Nervous System of Microstonum lineare (Turbella-bia, Macrostomida), Cell Tissue Res., 1980, vol. 211, pp. 31–40.
Corliss, J.B., Baross, J.A., and Hoffman, S.E., Submarine Hydrothermal Systems: A Probable Site for the Origin of Life, Ref. 80-7, Corvalis: School of Oceanography, Oregon State Univ., 1980.
Oster, C., Bellin, J.S., and Holmstrom, B., Pho-tochemistry of Riboflavin, Experientia, 1962, vol. 18, pp. 249–253.
Neverov, K.V., Mironov, E.V., Lyudnikova, T.A., Krasnovskii, A.A., Jr., and Kritsky, M.S., Phos-phorescence Analysis of Tri plet State of Pterins in Connection with their Photoreceptive Function in Biological Systems, Biokhimiya, 1996, vol. 61, pp. 1627–1635.
Lenci, F., Optical Absorption and Emission Spec-troscopy of Photoreceptor Pigments, Biophysics of Photoreceptors and Photomovements in Microorgan-isms, New York: Plenum, 1991, pp. 125–138.
Schuman, J.M., Schollnhammer, G., and Hemmerich, P., Intramolecular Addition of the Ribo-flavin Side Chain, Eur. J. Biochem., 1975, vol. 57, pp. 35–48.
Schollnhammer, G. and Hemmerich, P., Nucleo-philic Addition at the Photoexcited Flavin Cation: Synthesis and Properties of 6-and 9-Hydroxyflav-ocoenzyme Chromophores, Eur. J. Biochem., 1974, vol. 44, pp. 561–577.
Presti, D.E., The Photobiology of Carotenes and Flavins, The Biology of Photoreception, Cosens, D.J. and Vince-Ptice, D., Eds., Society of Experimen-tal Biology, 1983, pp. 133–180.
Ferris, J.F., Kuder, J.E., and Catalano, A.W., Photochemical Reactions and the Chemical Evo-lution of Purines and Nicotinamide Derivatives, Science, 1969, vol. 166, pp. 765–767.
Vierstra, R.D., Poff, K.L., Walker, E.B., and Song, P.-S., Effect of Xenon on the Excited States of Phototrophic Receptor Flavin in Corn Seedings, Plant. Physiol., 1981, vol. 67, pp. 996–998.
Krasnovskii, A.A., Chernysheva, E.K., and Kritsky, M.S., Study of the Role of Active Forms of Oxygen in the Flavin-Photosensitized NADH Oxidation, Biokhimiya, 1987, vol. 52, pp. 1474– 1483.
Cairns-Smith, A.G., Precambrian Solution Photo-chemistry, Inverse Segregation, and Baded Iron Formation, Nature, 1978, vol. 276, pp. 807–808.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kolesnikov, M.P., Kritsky, M.S. Study of Chemical Structure and of Photochemical Activity of Abiogenic Flavin Pigment. Journal of Evolutionary Biochemistry and Physiology 37, 507–514 (2001). https://doi.org/10.1023/A:1014026412183
Issue Date:
DOI: https://doi.org/10.1023/A:1014026412183