Enantioselective three-dimensional high-performance liquid chromatographic determination of amino acids in the Hayabusa2 returned samples from the asteroid Ryugu

Creators: Furusho, Aogu; Ishii, Chiharu; Akita, Takeyuki; Oyaide, Mai; Mita, Masashi; Naraoka, Hiroshi; Takano, Yoshinori; Dworkin, Jason P.; Oba, Yasuhiro; Koga, Toshiki; Fukushima, Kazuhiko; Aoki, Dan; Hashiguchi, Minako; Mita, Hajime; Chikaraishi, Yoshito; Ohkouchi, Naohiko; Ogawa, Nanako O.; Sakai, Saburo; Glavin, Daniel P.; Elsila, Jamie E.; Parker, Eric T.; Aponte, José C.; McLain, Hannah L.; Orthous-Daunay, Francois-Regis; Vuitton, Véronique; Thissen, Roland; Wolters, Cédric; Schmitt-Kopplin, Philippe; Ruf, Alexander; Isa, Junko; Hertkorn, Norbert; Eiler, John M.¹; Yoshimura, Toshihiro; Sugahara, Haruna; Graham, Heather V.; Furukawa, Yoshihiro; Araoka, Daisuke; Tanaka, Satoru; Yoshikawa, Takaaki; Kabashima, Fumie; Sasaki, Kazunori; Sato, Hajime; Yamazaki, Tomoya; Onose, Morihiko; Morita, Mayu; Kimura, Yuki; Kano, Kuniyuki; Aoki, Junken; Fujishima, Kosuke; Nomura, Shin-ichiro; Tachibana, Shogo; Nakamura, Tomoki; Noguchi, Takaaki; Okazaki, Ryuji; Yabuta, Hikaru; Yurimoto, Hisayoshi; Sakamoto, Kanako; Yada, Toru; Nishimura, Masahiro; Nakato, Aiko; Miyazaki, Akiko; Yogata, Kasumi; Abe, Masanao; Usui, Tomohiro; Yoshikawa, Makoto; Saiki, Takanao; Tanaka, Satoshi; Terui, Fuyuto; Nakazawa, Satoru; Okada, Tatsuaki; Watanabe, Sei-ichiro; Tsuda, Yuichi; Hamase, Kenji

1. California Institute of Technology

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.

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Acknowledgement

This study was partly supported by JSPS KAKENHI Grant Numbers JP22H02752, JP20H00202 and JP23H00148 and by NASA support of the Consortium for Hayabusa2 Analysis of Organic Solubles. The authors thank KAGAMI, Inc. (Osaka, Japan) for their technical support.

Contributions

Aogu Furusho: Writing – original draft, Investigation. Chiharu Ishii: Investigation. Takeyuki Akita: Investigation. Mai Oyaide: Investigation. Masashi Mita: Resources. Hiroshi Naraoka: Writing – review & editing, Investigation. Yoshinori Takano: Investigation, Resources. Jason P. Dworkin: Writing – review & editing, Resources. Yasuhiro Oba: Investigation, Resources. Toshiki Koga: Investigation, Resources. Kazuhiko Fukushima: Resources. Dan Aoki: Resources. Minako Hashiguchi: Resources. Hajime Mita: Resources. Yoshito Chikaraishi: Resources. Naohiko Ohkouchi: Resources. Nanako O. Ogawa: Resources. Saburo Sakai: Resources. Daniel P. Glavin: Resources. Jamie E. Elsila: Resources. Eric T. Parker: Resources. José C. Aponte: Resources. Hannah L. McLain: Resources. Francois-Regis Orthous-Daunay: Resources. Véronique Vuitton: Resources. Roland Thissen: Resources. Cédric Wolters: Resources. Philippe Schmitt-Kopplin: Resources. Alexander Ruf: Resources. Junko Isa: Resources. Norbert Hertkorn: Resources. John M. Eiler: Resources. Toshihiro Yoshimura: Resources. Haruna Sugahara: Resources. Heather V. Graham: Resources. Yoshihiro Furukawa: Resources. Daisuke Araoka: Resources. Satoru Tanaka: Resources. Takaaki Yoshikawa: Resources. Fumie Kabashima: Resources. Kazunori Sasaki: Resources. Hajime Sato: Resources. Tomoya Yamazaki: Resources. Morihiko Onose: Resources. Mayu Morita: Resources. Yuki Kimura: Resources. Kuniyuki Kano: Resources. Junken Aoki: Resources. Kosuke Fujishima: Resources. Shin-ichiro Nomura: Resources. Shogo Tachibana: Writing – review & editing, Resources. Tomoki Nakamura: Resources. Takaaki Noguchi: Resources. Ryuji Okazaki: Resources. Hikaru Yabuta: Resources. Hisayoshi Yurimoto: Resources. Kanako Sakamoto: Resources. Toru Yada: Resources. Masahiro Nishimura: Resources. Aiko Nakato: Resources. Akiko Miyazaki: Resources. Kasumi Yogata: Resources. Masanao Abe: Resources. Tomohiro Usui: Resources. Makoto Yoshikawa: Resources. Takanao Saiki: Resources. Satoshi Tanaka: Resources. Fuyuto Terui: Resources. Satoru Nakazawa: Resources. Tatsuaki Okada: Resources. Sei-ichiro Watanabe: Resources. Yuichi Tsuda: Resources. Kenji Hamase: Writing – review & editing, Supervision.

Data Availability

Appendix. Supplementary materials

Conflict of Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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