(2S)-2-Amino-5-chloro-4-hydroxy-5-hexenoic acid,a new chloroamino acid,and related compounds fromAmanita gymnopus |
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| Authors: | Hatanaka Shin-Ichi Furukawa Jun Aoki Toshio Akatsuka Hirokazu Nagasawa Eiji |
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| Institution: | (1) Department of Biology, Division of Natural Sciences, International Christian University, 3-10-2, Osawa chome, Mitaka-shi, 181 Tokyo, Japan;(2) Exploratory Research Laboratories II, Daiichi Pharmaceutical Co. Ltd., 1-16-13, Kita-kasai, Edogawa-ku, 134 Tokyo, Japan;(3) Iwate Biotechnology Research Center, 22-174-4, Narita, Kitakami-shi, 024 Iwate Prefecture, Japan;(4) Network Engineering Department, Service Engineering Headquarters, Nippon Telegraph and Telephone Corporation, 1-1-6, Uchisaiwai-cho, Chiyoda-ku, 100-19 Tokyo, Japan;(5) Tottori Mycological Institute, 211, Kokoge, Tottori-shi, 681-11 Tottori, Japan |
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| Abstract: | Combining different chromatography systems, unusual nonprotein amino acids were isolated and unequivocally identified from a small amount (less than 100 g fresh weight) ofAmanita gymnopus fruit body. Without obtaining crystals of these amino acids, on the basis of1H-NMR determination, high resolution mass spectrometry, chlorine analysis and oxidation with L-amino acid oxidase, one of them proved to be a new chloroamino acid, (2S)-2-amino-5-chloro-4-hydroxy-5-hexenoic acid (G2). The other three were (2S)-2-amino-5-hexenoic acid (G1), (2S)-2-amino-4,5-hexadienoic acid (G3) and (2S)-2-amino-5-hexynoic acid (G4). Amino acid (G1) was also encountered for the first time in natural products. Amino acid (G3) has been reported from several kinds of fungi belonging toAmanita, subgenusLepidella. The occurrence of amino acid (G4) was already reported fromCortinarius claricolor.Part 23 in the series  Biochemical studies of nitrogen compounds in fungi. Part 22, Hatanaka, S. I. et al. 1985. Trans. Mycol. Soc. Japan26: 61–68. |
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| Keywords: | Amanita gymnopus (2S)-2-amino-5-chloro-4-hydroxy-5-hexenoic acid (2S)-2-amino-5-hexynoic acid (2S)-2-amino-5-hexynoic acid non-protein amino acids |
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