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Sci., 149, 222\u2013224 (1909)."},{"key":"r9","unstructured":"9) Barger, G., and Ewins, A. J., CCLVII. \u2014 The constitution of ergothioneine: a betaine related to histidine. J. Chem. Soc., 99, 2336\u20132341 (1911)."},{"key":"r10","unstructured":"10) Fugmann, B., and Steglich, W., Unusual components of the toadstool Lyophyllum connatum (agaricales). Angew. Chem. Int. Ed. Engl., 23, 72\u201373 (1984)."},{"key":"r11","unstructured":"11) Melville, D. B., Genghof, D. S., Inamine, E., and Kovalenko, V., Ergothioneine in microorganisms. J. Biol. Chem., 223, 9\u201317 (1956)."},{"key":"r12","unstructured":"12) Melville, D. B., Horner, W. H., and Lubschez, R., Tissue ergothioneine. J. Biol. Chem., 206, 221\u2013228 (1954)."},{"key":"r13","unstructured":"13) Melville, D. B., Horner, W. H., Otken, C. C., and Ludwig, M. L., Studies on the origin of ergothioneine in animals. J. Biol. Chem., 213, 61\u201368 (1955)."},{"key":"r14","unstructured":"14) Behre, J. A., and Benedict, S. R., The occurrence and determination of thioneine (ergothioneine) in human blood. J. Biol. Chem., 82, 11\u201315 (1929)."},{"key":"r15","unstructured":"15) Melville, D. B., and Eich, S., The occurrence of ergothioneine in plant material. J. Biol. Chem., 218, 647\u2013651 (1956)."},{"key":"r16","unstructured":"16) Dahl, T. A., Midden, W. R., and Hartman, P. E., Some prevalent biomolecules as defenses against singlet oxygen damage. Photochem. Photobiol., 47, 357\u2013362 (1988)."},{"key":"r17","unstructured":"17) Akanmu, D., Cecchini, R., Aruoma, O. I., and Halliwell, B., The antioxidant action of ergothioneine. Arch. Biochem. Biophys., 288, 10\u201316 (1991)."},{"key":"r18","unstructured":"18) Aruoma, O. I., Whiteman, M., England, T. G., and Halliwell, B., Antioxidant action of ergothioneine: assessment of its ability to scavenge peroxynitrite. Biochem. Biophys. Res. Commun., 231, 389\u2013391 (1997)."},{"key":"r19","unstructured":"19) Rigaku, CrystalClear, Rigaku Corporation, 3-9-12 Akishima, Tokyo, Japan (2000)."},{"key":"r20","unstructured":"20) Sheldrick, G. M. \u201cSHELXL97 and SHELXS97\u201d, University of G\u00f6ttingen, Germany (1997)."},{"key":"r21","doi-asserted-by":"crossref","unstructured":"21) Flack, H. D., On enantiomorph-polarity estimation. Acta Crystallor., A39, 876\u2013881 (1983).","DOI":"10.1107\/S0108767383001762"},{"key":"r22","unstructured":"22) Suda, I., Kosanka kinou. In \u201cShokuhin Kinou Kenkyuho\u201d (in Japanese), eds. Shinohara, K., Suzuki, T., and Kaminogawa, S., Korin, Tokyo, pp. 218\u2013220 (2000)."},{"key":"r23","unstructured":"23) Matsuda, H., Ninomiya, K., Shimoda, H., and Yoshikawa, M., Hepatoprotective principles from the flowers of Tilia argentea (Linden): structure requirement of Tiliroside and mechanisms of action. Bioorg. Med. Chem., 10, 707\u2013712 (2002)."},{"key":"r24","unstructured":"24) Matsumoto, K., Transaminase. In \u201cProtein, Nucleic and Enzyme\u201d (in Japanese), eds. Ogata, K., Inoue, T., and Matsumoto, K., Kyoritsu, Tokyo, pp. 94\u201398 (1981)."},{"key":"r25","doi-asserted-by":"crossref","unstructured":"25) Taraz, K., Weber, M., and Budzikiewicz, H., Synthesis of the stereoisomers of b-hydroxyhistidine and their analytical identification in hydrolysates of bacterial peptides. Z. Naturforsch., 53b, 1520\u20131524 (1998).","DOI":"10.1515\/znb-1998-1216"},{"key":"r26","unstructured":"26) Farrugia, L. J. ORTEP-3 for Windows \u2014 a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr., 30, 565 (1997)."},{"key":"r27","doi-asserted-by":"crossref","unstructured":"27) Sugihara, A., Uemura, K., Matsuura, Y., Tanaka, N., Ashida, T., and Kakudo, M., The crystal structure of L-ergothioneine dihydrate, C9H15N3O2S\u00b72H2O. Acta Crystallogr., B32, 181\u2013185 (1976).","DOI":"10.1107\/S0567740876002550"},{"key":"r28","unstructured":"28) Zinner, G., and Isensee, G., Darstellung und Acylierungen von 1.1-Dialkyl-3-hydroxyharnstoffen. Arch. Pharm., 307, 7\u201312 (1974)."},{"key":"r29","unstructured":"29) Hartman, P. E. [32] Ergothioneine as antioxidant. Meth. Enzy., 186, 310\u2013318 (1990)."},{"key":"r30","unstructured":"30) Melville, D. B., Ergothioneine. Vitam. Horm., 17, 155\u2013204 (1959)."},{"key":"r31","doi-asserted-by":"crossref","unstructured":"31) Konno, K., Shirahama, H., and Matsumoto, T., Clithioneine, an amino acid betaine from Clitocybe acromelalga. Phytochemistry, 23, 1003\u20131006 (1984).","DOI":"10.1016\/S0031-9422(00)82600-X"},{"key":"r32","unstructured":"32) Matsuo, M., Sato, K., and Kitani, S., Isolation and structure of sclerothionine, a metabolite of Sclerotinia fungus. Agric. Biol. Chem., 31, 353\u2013356 (1967)."},{"key":"r33","unstructured":"33) Ishikawa, Y., and Melville, D. 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