Journal of Chromatography Open (May 2024)
Enantioselective three-dimensional high-performance liquid chromatographic determination of amino acids in the Hayabusa2 returned samples from the asteroid Ryugu
- Aogu Furusho,
- Chiharu Ishii,
- Takeyuki Akita,
- Mai Oyaide,
- Masashi Mita,
- Hiroshi Naraoka,
- Yoshinori Takano,
- Jason P. Dworkin,
- Yasuhiro Oba,
- Toshiki Koga,
- Kazuhiko Fukushima,
- Dan Aoki,
- Minako Hashiguchi,
- Hajime Mita,
- Yoshito Chikaraishi,
- Naohiko Ohkouchi,
- Nanako O. Ogawa,
- Saburo Sakai,
- Daniel P. Glavin,
- Jamie E. Elsila,
- Eric T. Parker,
- José C. Aponte,
- Hannah L. McLain,
- Francois-Regis Orthous-Daunay,
- Véronique Vuitton,
- Roland Thissen,
- Cédric Wolters,
- Philippe Schmitt-Kopplin,
- Alexander Ruf,
- Junko Isa,
- Norbert Hertkorn,
- John M. Eiler,
- Toshihiro Yoshimura,
- Haruna Sugahara,
- Heather V. Graham,
- Yoshihiro Furukawa,
- Daisuke Araoka,
- Satoru Tanaka,
- Takaaki Yoshikawa,
- Fumie Kabashima,
- Kazunori Sasaki,
- Hajime Sato,
- Tomoya Yamazaki,
- Morihiko Onose,
- Mayu Morita,
- Yuki Kimura,
- Kuniyuki Kano,
- Junken Aoki,
- Kosuke Fujishima,
- Shin-ichiro Nomura,
- Shogo Tachibana,
- Tomoki Nakamura,
- Takaaki Noguchi,
- Ryuji Okazaki,
- Hikaru Yabuta,
- Hisayoshi Yurimoto,
- Kanako Sakamoto,
- Toru Yada,
- Masahiro Nishimura,
- Aiko Nakato,
- Akiko Miyazaki,
- Kasumi Yogata,
- Masanao Abe,
- Tomohiro Usui,
- Makoto Yoshikawa,
- Takanao Saiki,
- Satoshi Tanaka,
- Fuyuto Terui,
- Satoru Nakazawa,
- Tatsuaki Okada,
- Sei-ichiro Watanabe,
- Yuichi Tsuda,
- Kenji Hamase
Affiliations
- Aogu Furusho
- Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan; School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan
- Chiharu Ishii
- Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan
- Takeyuki Akita
- Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan
- Mai Oyaide
- Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan
- Masashi Mita
- KAGAMI, Inc., Osaka 567-0085, Japan
- Hiroshi Naraoka
- Department of Earth and Planetary Sciences, Kyushu University, Fukuoka 819-0395, Japan
- Yoshinori Takano
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Jason P. Dworkin
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- Yasuhiro Oba
- Institute of Low Temperature Science, Hokkaido University, Sapporo 060-0189, Japan
- Toshiki Koga
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Kazuhiko Fukushima
- Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan
- Dan Aoki
- Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan
- Minako Hashiguchi
- Graduate School of Environmental Studies, Nagoya University, Nagoya 464-8601, Japan
- Hajime Mita
- Department of Life, Environment and Applied Chemistry, Fukuoka Institute of Technology, Fukuoka 811-0295, Japan
- Yoshito Chikaraishi
- Institute of Low Temperature Science, Hokkaido University, Sapporo 060-0189, Japan
- Naohiko Ohkouchi
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Nanako O. Ogawa
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Saburo Sakai
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Daniel P. Glavin
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- Jamie E. Elsila
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- Eric T. Parker
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- José C. Aponte
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- Hannah L. McLain
- Solar System Exploration Division, NASA Goddard Space Flight Center, Greenbelt, MD 20771, United States
- Francois-Regis Orthous-Daunay
- Institut de Planetologie et d'Astrophysique de Grenoble, University Grenoble Alpes, 38000 Grenoble, France
- Véronique Vuitton
- Institut de Planetologie et d'Astrophysique de Grenoble, University Grenoble Alpes, 38000 Grenoble, France
- Roland Thissen
- Institut Chimie Physique, CNRS, University of Paris-Saclay, 91405 Orsay, France
- Cédric Wolters
- Institut de Planetologie et d'Astrophysique de Grenoble, University Grenoble Alpes, 38000 Grenoble, France
- Philippe Schmitt-Kopplin
- Analytical BioGeoChemistry, Helmholtz Munich, 85764 Neuherberg, Germany
- Alexander Ruf
- Laboratoire de Physique des Interactions Ioniques et Moléculaires, Université Aix-Marseille, 13397 Marseille, France
- Junko Isa
- Earth-Life Science Institute, Tokyo Institute of Technology, Tokyo 152-8550, Japan
- Norbert Hertkorn
- Analytical BioGeoChemistry, Helmholtz Munich, 85764 Neuherberg, Germany
- John M. Eiler
- Division of Geological and Planetary Sciences, California Institute of Technology, Pasadena, CA 91125, United States
- Toshihiro Yoshimura
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Haruna Sugahara
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Heather V. Graham
- Biogeochemistry Research Center, Japan Agency for Marine-Earth Science and Technology, Yokosuka 237-0061, Japan
- Yoshihiro Furukawa
- Department of Earth Science, Tohoku University, Sendai 980-8578, Japan
- Daisuke Araoka
- Geological Survey of Japan, National Institute of Advanced Industrial Science and Technology, Tsukuba 305-8567, Japan
- Satoru Tanaka
- Horiba Techno Service Co., Ltd., Kyoto 601-8510, Japan
- Takaaki Yoshikawa
- Horiba Advanced Techno, Co., Ltd., Kyoto 601-8510, Japan
- Fumie Kabashima
- LECO Japan Corporation, Tokyo 105-0014, Japan
- Kazunori Sasaki
- Human Metabolome Technologies, Inc., Tsuruoka 997-0052, Japan
- Hajime Sato
- Human Metabolome Technologies, Inc., Tsuruoka 997-0052, Japan
- Tomoya Yamazaki
- Institute of Low Temperature Science, Hokkaido University, Sapporo 060-0189, Japan
- Morihiko Onose
- Horiba Techno Service Co., Ltd., Kyoto 601-8510, Japan
- Mayu Morita
- Horiba Techno Service Co., Ltd., Kyoto 601-8510, Japan
- Yuki Kimura
- Institute of Low Temperature Science, Hokkaido University, Sapporo 060-0189, Japan
- Kuniyuki Kano
- Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo 113-0033, Japan
- Junken Aoki
- Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo 113-0033, Japan
- Kosuke Fujishima
- Earth-Life Science Institute, Tokyo Institute of Technology, Tokyo 152-8550, Japan
- Shin-ichiro Nomura
- Department of Robotics, Tohoku University, Sendai 980-8579, Japan
- Shogo Tachibana
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; Department of Earth and Planetary Science, University of Tokyo, Tokyo 113-0033, Japan
- Tomoki Nakamura
- Department of Earth Science, Tohoku University, Sendai 980-8578, Japan
- Takaaki Noguchi
- Division of Earth and Planetary Sciences, Kyoto University, Kyoto 606-8502, Japan
- Ryuji Okazaki
- Department of Earth and Planetary Sciences, Kyushu University, Fukuoka 819-0395, Japan
- Hikaru Yabuta
- Department of Earth and Planetary Systems Science, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
- Hisayoshi Yurimoto
- Department of Earth and Planetary Sciences, Hokkaido University, Sapporo 060-0810, Japan
- Kanako Sakamoto
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Toru Yada
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Masahiro Nishimura
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Aiko Nakato
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; Antarctic Meteorite Research Center, National Institute of Polar Research, Tachikawa 190-8518, Japan
- Akiko Miyazaki
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Kasumi Yogata
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Masanao Abe
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; School of Physical Sciences, The Graduate University for Advanced Studies, Hayama 240-0193, Japan
- Tomohiro Usui
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Makoto Yoshikawa
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; School of Physical Sciences, The Graduate University for Advanced Studies, Hayama 240-0193, Japan
- Takanao Saiki
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Satoshi Tanaka
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; School of Physical Sciences, The Graduate University for Advanced Studies, Hayama 240-0193, Japan
- Fuyuto Terui
- Department of Mechanical Engineering, Kanagawa Institute of Technology, Atsugi 243-0292, Japan
- Satoru Nakazawa
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Tatsuaki Okada
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan; Department of Chemistry, University of Tokyo, Tokyo 113-0033, Japan
- Sei-ichiro Watanabe
- Graduate School of Environmental Studies, Nagoya University, Nagoya 464-8601, Japan
- Yuichi Tsuda
- Institute of Space and Astronautical Science, Japan Aerospace Exploration Agency (JAXA), Sagamihara 252-5210, Japan
- Kenji Hamase
- Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan; Corresponding author.
- Journal volume & issue
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Vol. 5
p. 100134
Abstract
The chirality of amino acids in extraterrestrial materials may provide an insight into the origin of the essential l-enantiopure amino acids in the terrestrial biosphere. In 2020, the Hayabusa2 mission succeeded in bringing back surface materials from the C-type asteroid (162173) Ryugu to the Earth. Amino acids were one of the targeted organic molecules to be studied in the Ryugu samples. To analyze the various structural isomers of amino acids, which were expected to be present, from the limited amount of the returned samples, the development of a highly-sensitive and selective analytical method was necessary. In the present study, a three-dimensional high-performance liquid chromatography (3D-HPLC) system has been developed for the enantioselective determination of five proteinogenic and three non-proteinogenic amino acids in the Ryugu samples, in which amino acids in the sample were separated by reversed-phase, anion-exchange and enantioselective columns after the fluorescence derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiozole. The applicability of the analytical system to the extraterrestrial samples was evaluated by analyzing several types of carbonaceous meteorites before applying the system to the Ryugu samples. In the analysis of the Ryugu samples, all of the target amino acids were successfully determined quantitatively. Non-proteinogenic amino acids including 2-amino-n-butyric acid, isovaline and norvaline, rarely present in the terrestrial environment, were found as almost racemic mixtures with 47.1 to 55.2%l.
