Summary
Histidyl-histidine (His-His) has been synthesized in a yield of up to 14.4% under plausible prebiotic conditions using histidine (His), cyanamide, and 4-amino-5-imidazole carboxamide. A trace amount of His trimer was also detected. Because the imidazole group of His is involved in a number of important enzymatic reactions, and His-His has been shown to catalyze the prebiotic synthesis of glycyl-glycine, we expect this work will stimulate further studies on the catalytic activities of simple His-containing peptides in prebiotic reactions.
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References
Hawker JR, Oró J (1981) Cyanamide mediated synthesis of peptides containing histidine and hydrophobic amino acids. J Mol Evol 17:285–294
Hulshof J, Ponnamperuma C (1976) Prebiotic condensation reactions in an aqueous medium: a review of condensing agents. Origins Life 7:197–224
Ibanez J, Kimball AP, Oró J (1971) The effect of imidazole, cyanamide, and polyornithine on the condensation of nucleotides in aqueous system. In: Buvet R, Ponnamperuma C (eds) Chemical evolution and origin of life. North Holland, Amsterdam, pp 171–179
Kenyon DH, Steinman G (1969) Biochemical predestination. McGraw-Hill, New York
Lazcano A (1986) Prebiotic evolution and the origin of cells. Treballs Soc Cat Biol 39:73–103
Lazcano A, Fastag J, Gariglio P, Ramirez C, Oró J (1988) On the early evolution of RNA polymerase. J Mol Evol 27:365–376
Lundanes E, Greibrokk T (1984) Retention of dipeptides in reversed-phase HPLC. In: Hancock WS (ed) Handbook of HPLC for the separation of amino acids, peptides and proteins. CRC Press, Boca Raton, Florida, pp 49–52
Nakamura H (1977) Thin-layer chromatography of histidine, histamine and histidyl peptides at picomole level using a unique fluorogenic reaction with fluorescamine. J Chromatogr 131: 215–222
Nooner DW, Oró J (1974) Direct synthesis of polypeptides. J Mol Evol 3:79–88
Nooner DW, Sherwood E, More MA, Oró J (1977) Cyanamide mediated synthesis under plausible primitive earth conditions. J Mol Evol 10:211–220
Oró J, Kimball AP (1962) Synthesis of purines under possible primitive Earth conditions II. Purine intermediates from hydrogen cyanide. Arch Biochem Biophys 96:293–313
Oró J, Lazcano A (1984) A minimal living system and the origin of a protocell. Adv Space Res 4:167–176
Oró J, Basile B, Cortes S, Shen C, Yamrom T (1984) The prebiotic synthesis and catalytic role of imidazoles and other condensing agents. Origins Life 14:237–242
Rabinowitz J, Hampai A (1985) Quantitative polyphosphateinduced “prebiotic” peptide formation in H2O by addition of certain azoles and ions. J Mol Evol 21:199–201
Robin Y (1964) Biological distribution of guanidines and phosphagens in marine annelida and related phyla from California, with a note on pluriphosphagens. Comp Biochem Physiol 12: 347–367
Shen C, Yang L, Miller SL, Oró J (1987) Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Origins Life 17:295–305
Shen C, Yang L, Miller SL, Oró J (1990a) Prebiotic synthesis of histidine. J Mol Evol 31:167–174
Shen C, Lazcano A, Oró J (1990b) Enhancing effects of histidylhistidine in some prebiotic reactions. J Mol Evol (in press)
Steinman G, Kenyon DH, Calvin M (1966) The mechanism and protobiological relevance of dicyanamide-mediated peptide synthesis. Biochim Biophys Acta 124:339–350
Udenfried S, Stein S, Bohlen P, Dairman W, Leimgruber W, Weigele M (1972) Fluorescamine: a reagent for assay of amino acids, peptides, proteins in the picomole range. Science 178:871–873
Weber AL, Caroon JM, Warden JT, Lemmon RM, Calvin M (1977) Simultaneous peptide and oligonucleotide formation in mixtures of amino acid, nucleoside triphosphate, imidazole, and magnesium ion. BioSystems 8:277–286
White DH, Erickson JC (1980) Catalysis of peptide bond formation by histidyl-histidine in a fluctuating clay environment. J Mol Evol 16:279–290
White DH, Erickson JC (1981) Histidyl-histidine catalysis of glycine condensation in fluctuating clay enviroments. In: Wolman Y (ed) Origins of life. Reidel, Dordrecht, Holland, pp 393–397
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Shen, C., Mills, T. & Oró, J. Prebiotic synthesis of histidyl-histidine. J Mol Evol 31, 175–179 (1990). https://doi.org/10.1007/BF02109493
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DOI: https://doi.org/10.1007/BF02109493