Development of enantiomer-specific isotope analysis (ESIA) of amino acids

2009 Fiscal Year Final Research Report

• Project/Area Number: 20740316
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Geochemistry/Astrochemistry
• Research Institution: Japan Agency for Marine-Earth Science and Technology
• Principal Investigator: TAKANO Yoshinori Japan Agency for Marine-Earth Science and Technology, 海洋・極限環境生物圏領域, 研究員 (80399815)
• Co-Investigator(Renkei-kenkyūsha): OHKOUCHI Naohiko 独立行政法人海洋研究開発機構, 海洋・極限環境生物圏領域, プログラムディレクター (00281832) ; CHIKARAISHI Yoshito 独立行政法人海洋研究開発機構, 海洋・極限環境生物圏領域, 研究員 (50455490)
• Project Period (FY): 2008 – 2009
• Keywords: アミノ酸 / エナンチオマー / 安定同位体比 / 生物プロセス / 非生物プロセス

Research Abstract

生体を構成する分子には、光学異性体や構造異性体が存在する。身近な光学異性体の例でいうと、タンパク質を構成するアミノ酸は、基本的にL-体アミノ酸から構成され、核酸の糖は、D-体リボースから構成されることが挙げられる。また、D-アラニンなどのようにタンパク質は構成しないが、細胞内のペプチドグリカンとして局所的に高濃度に存在する場合がある。これらの他にも生体内で生理活性を持つ種々の分子は、いずれかの異性体に偏っていることが多い。本研究では、従来のキラルなキャピラリーカラムを用いた光学異性体の分離ではなく、光学活性アルコール付加によるジアステレオマー誘導体化法を導入し、自然界に存在する光学異性体および構造異性体の個々の分子レベル窒素同位体比の評価を行った。

Research Products

• [Journal Article] Biogeography and biodiversity in sulfide structures of active and inactive vents at deep-sea hydrothermal fields of the Southern Mariana Trough. (2010)
  • Author(s): Kato, S., Takano, Y., Kakegawa, T., Oba, H., Inoue, K., Kobayashi, C., Utsumi, M., Marumo, K., Kobayashi, K., Ito, Y., Ishibashi, J., Yamagishi, A.
  • Journal Title: Applied and Environmental Microbiology 76 Pages: 2968-2979
  • URL: DOI:10.1128/AEM.00478-10
  • Peer Reviewed
• [Journal Article] Amino acid trophic level (ATL): elucidation of aquatic food web structure based on compound-specific nitrogen isotopic composition of amino acids. (2009)
  • Author(s): Chikaraishi, Y., Ogawa, O.N., Kashiyama, Y., Takano, Y., Suga, H., Tomitani, A., Miyashita, H., Kitazato, H., Ohkouchi, N.
  • Journal Title: Limnology and Oceanography: Method 7 Pages: 740-750
  • Peer Reviewed
• [Journal Article] Abundance of Zetaproteobacteria within crustal fluids in back-arc hydrothermal fields of the Southern Mariana Trough. (2009)
  • Author(s): Kato, S., Yanagawa, K., Sunamura, M., Takano, Y., Ishibashi, J. -I., Kakegawa, T., Utsumi, M., Yamanaka, T., Toki, T., Noguchi, T., Kobayashi, K., Moroi, A., Kimura, H., Kawarabayasi, Y., Marumo, K., Urabe, T., Yamagishi, A.
  • Journal Title: Environmental Microbiology 11 Pages: 3210-3222
  • Peer Reviewed
• [Journal Article] Microbial community structure, pigment composition, and nitrogen source of red snow in Antarctica. (2009)
  • Author(s): Fujii, M., Takano, Y., Kojima, H., Hoshino, T., Tanaka, R., Fukui, M.
  • Journal Title: Microbial Ecology
  • URL: DOI10.1007/s00248-009-9594-9.
  • Peer Reviewed
• [Journal Article] アミノ酸(N-ピバロイル-イソプロピルエステル誘導体)のGC/MSによる解析. (2009)
  • Author(s): 力石嘉人, 高野淑識, 大河内直彦
  • Journal Title: Researches in Organic Geochemistry 25 Pages: 61-70
  • Peer Reviewed
• [Journal Article] Organic analysis of peridotite rocks from Ashadze and Logatchev hydrothermal sites. (2009)
  • Author(s): Bassez, M-P., Takano, Y., Ohkouchi, N.
  • Journal Title: International Journal of Molecular Sciences 10 Pages: 2986-2998
  • Peer Reviewed
• [Journal Article] Compound-specific nitrogen isotope analysis of D-alanine, L-alanine, and valine: application of diastereomer separation toδ15N and microbial peptidoglycan studies. (2009)
  • Author(s): Takano, Y., Chikaraishi, Y., Ogawa, O.N., Kitazato, H., Ohkouchi, N.
  • Journal Title: Analytical Chemistry 81 Pages: 394-399
  • Peer Reviewed
• [Journal Article] Evidence for the global distribution of Chlorophyll-d. (2008)
  • Author(s): Kashiyama, Y., Miyashita, H., Ohkubo, S., Ogawa, O.N., Chikaraishi, Y., Takano, Y., Suga, H., Toyohuku, T., Nomaki, H., Kitazato, H., Nagata, T., Ohkouchi, N.
  • Journal Title: Science 321 Pages: 658-658
  • Peer Reviewed
• [Journal Article] Pore pressure penetrometers document high overpressure near the seafloor where multiple submarine landslides have occurred on the continental slope, offshore Louisiana, Gulf of Mexico. (2008)
  • Author(s): Flemings, P.B., Long H., Dugan B., Germaine J., John C.M., Behrmann J.H., Sawyer D., IODP Expedition 308 Scientists
  • Journal Title: Earth and Planetary Science Letters 269 Pages: 309-325
  • Peer Reviewed
• [Journal Article] 物質進化と極限環境の地下生物圏に関する有機地球化学的研究 (2008)
  • Author(s): 高野淑識
  • Journal Title: 地球化学 42 Pages: 23-40
  • Peer Reviewed
• [Journal Article] Mineralogy and isotope geochemistry of active submarine hydrothermal field at Suiyo Seamount, Izu-Bonin Arc, West Pacific Ocean. (2008)
  • Author(s): Marumo, K., Urabe, T., Goto, A., Takano, Y., Nakasheama, M.
  • Journal Title: Resource Geology 58 Pages: 220-248
  • URL: doi:10.1017/S1743921308022199
  • Peer Reviewed
• [Presentation] 海底堆積物中の古細菌が生きている直接の証拠 (2009)
  • Author(s): 高野淑識, 力石嘉人, 小川奈々子, 野牧秀隆, 大河内直彦
  • Organizer: 日本地球化学会
  • Place of Presentation: 広島
  • Year and Date: 2009-09-15
• [Presentation] 海洋地殻流体中のZetaproteobacteriaとその重要性 (2009)
  • Author(s): 加藤真吾, 柳川勝紀, 砂村倫成, 高野淑識, 石橋純一郎, 浦辺徹郎, 他
  • Organizer: 日本地球化学会
  • Place of Presentation: 広島
  • Year and Date: 2009-09-15
• [Presentation] Nitrogen isotopic compositions of amino acids from microorganisms as a tool for studying microbial processes. (2009)
  • Author(s): Yamaguchi, Y.T., Y. Takano, Y. Chikaraishi, Y. Yokoyama, N. Ohkouchi
  • Organizer: 19th International Symposium on Environmental Biogeochemistry
  • Place of Presentation: Humburg
  • Year and Date: 2009-09-14
• [Presentation] Alkenones in sediments from freshwater and saline lakes on the Skarvsnes area, Antarctica (2009)
  • Author(s): M. Takeda, K. Sawada, Y. Takano
  • Organizer: 24th International Meeting on Organic Geochemistry Bremen
  • Place of Presentation: Organic Geochemistry Bremen
  • Year and Date: 2009-09-08
• [Presentation] Elucidation of food web structures based on compound-specific nitrogen isotopic composition of amino acids (2009)
  • Author(s): Yoshito Chikaraishi, Nanako O. Ogawa, Yuichiro Kashiyama, Yoshinori Takano, Yasuhiko Yamaguchi, Hiroshi Kitazato, Naohiko Ohkouchi
  • Organizer: 24th International Meeting on Organic Geochemistry Bremen
  • Place of Presentation: Organic Geochemistry Bremen
  • Year and Date: 2009-09-08
• [Presentation] Enantiomer-specific isotope analysis (ESIA) of D- and L-alanine for nitrogen isotopic composition (15N/14N) in bacterial and chemical processes (2009)
  • Author(s): Y. Takano, Y. Chikaraishi, N.O. Ogawa, N. Ohkouchi
  • Organizer: 24th International Meeting on Organic Geochemistry Bremen
  • Place of Presentation: Organic Geochemistry Bremen
  • Year and Date: 2009-09-07
• [Presentation] In-situ 13C-tracer experiments for deep-sea benthic Archaea: evidence of active metabolism by membrane lipid biomarkers (2009)
  • Author(s): Y. Takano, N.O. Ogawa, H. Nomaki, Y. Chikaraishi, H. Kitazato, N. Ohkouchi
  • Organizer: 24th International Meeting on Organic Geochemistry
  • Place of Presentation: Bremen
  • Year and Date: 2009-09-07
• [Presentation] 生きている指標とされるIntact Polar Lipidsとその地球化学的意味 (2009)
  • Author(s): 高野淑識, Julius Lipp, 山口保彦, Kai-Uwe Hinrichs, 大河内直彦
  • Organizer: 日本有機地球化学会
  • Place of Presentation: 松江
  • Year and Date: 2009-08-05
• [Presentation] 地下生物圏の生細胞識別法および代謝活性評価法の開発:シグナルを分子レベルで分ける (2009)
  • Author(s): 高野淑識, 小川奈々子, 力石嘉人, 大河内直彦
  • Organizer: 地球惑星科学連合大会
  • Place of Presentation: 幕張
  • Year and Date: 2009-05-23
• [Presentation] 微生物のアミノ酸窒素同位体組成:微生物食物連鎖の解明へ向けて (2009)
  • Author(s): 山口保彦, 高野淑識, 力石嘉人, 大河内直彦
  • Organizer: 地球惑星科学連合大会
  • Place of Presentation: 幕張
  • Year and Date: 2009-05-23
• [Presentation] 「アミノ酸栄養段階」古食性解析に向けた殻体内アミノ酸同位体分析法の開発 (2009)
  • Author(s): 柏山祐一郎, 力石嘉人, 高野淑識, 小川奈々子, 北里洋, 大河内直彦
  • Organizer: 日本古生物学会
  • Place of Presentation: 沖縄
  • Year and Date: 2009-02-01
• [Presentation] In-situ tracer experiment for benthic archaea: carbon isotopic evidence of active metabolism from caldarchaeol and crenarchaeol of archaeal membrane lipids (2008)
  • Author(s): Yoshinori Takano, Hidetaka Nomaki, Nanako O. Ogawa, Yoshito Chikaraishi, Hiroshi Kitazato, Naohiko Ohkouchi
  • Organizer: 7th International Symposium for Subsurface Microbiology (ISSM)
  • Place of Presentation: Shizuoka
  • Year and Date: 2008-11-16
• [Presentation] Site-specific 13C/12C analysis of alanine by NMR (2008)
  • Author(s): Y.C. Saigusa, Y. Chikaraishi, Y. Takano, H. Kitazato, N. Ohkouchi
  • Organizer: 4th International Symposium on Isotopomers (ISI)
  • Place of Presentation: Tokyo
  • Year and Date: 2008-10-05
• [Presentation] 分子レベルから立体異性体分子レベル窒素同位体比への展開 (2008)
  • Author(s): 高野淑識, 力石嘉人, 小川奈々子, 北里洋, 大河内直彦
  • Organizer: 2008年度日本地球化学会
  • Place of Presentation: 駒場
  • Year and Date: 2008-09-18
• [Presentation] 海底での同位体トレーサー培養実験からみた古細菌の代謝活性 (2008)
  • Author(s): 高野淑識, 野牧秀隆, 小川奈々子, 力石嘉人, 稲垣史生, 北里洋, 大河内直彦
  • Organizer: 2008年度日本地球化学会
  • Place of Presentation: 駒場
  • Year and Date: 2008-09-18
• [Presentation] アミノ酸の窒素同位体比分析を用いた北海道縄文時代人の食性解析 (2008)
  • Author(s): 内藤裕一, Noah V. Honch, 大河内直彦, 小川奈々子, 力石嘉人, 高野淑識, 柏山祐一郎, 米田穣
  • Organizer: 2008年度日本地球化学会
  • Place of Presentation: 駒場
  • Year and Date: 2008-09-18
• [Presentation] アミノ酸の窒素同位体比を用いた食物連鎖解析 (2008)
  • Author(s): 力石嘉人, 小川奈々子, 柏山祐一郎, 高野淑識, 北里洋, 大河内直彦
  • Organizer: 2008年度日本地球化学会
  • Place of Presentation: 駒場
  • Year and Date: 2008-09-18
• [Presentation] 原核生物のペプチドグリカンに含まれるD-, L-アラニンの立体異性体分子レベル窒素同位体比 (2008)
  • Author(s): 高野淑識, 力石嘉人, 小川奈々子, 北里洋, 大河内直彦
  • Organizer: 2008年度日本有機地球化学会
  • Place of Presentation: 名古屋
  • Year and Date: 2008-07-24
• [Presentation] Application of NMR to characterize intact polar lipids in deep biosphere (2008)
  • Author(s): Yoshinori Takano, Fumio Inagaki, Yuki Morono, Nanako O. Ogawa, Hiroshi Kitazato, Naohiko Ohkouchi
  • Organizer: Goldschmidt conference
  • Place of Presentation: Vancover, Canada
  • Year and Date: 2008-07-15
• [Presentation] アミノ酸の窒素同位体比を用いた新しい古食性解析法:応用と展望 (2008)
  • Author(s): 柏山祐一郎, 力石嘉人, 高野淑識, 小川奈々子, 北里洋, 大河内直彦, 冨田武照, 棚部一成
  • Organizer: 2008年古生物学会年会
  • Place of Presentation: 仙台
  • Year and Date: 2008-07-05
• [Presentation] アミノ酸の窒素同位体比を用いた新しい古食性解析法:原理 (2008)
  • Author(s): 大河内直彦, 力石嘉人, 小川奈々子, 柏山祐一郎, 高野淑識, 北里洋
  • Organizer: 2008年古生物学会年会
  • Place of Presentation: 仙台
  • Year and Date: 2008-07-05
• [Book] Earth, Life, and Isotopes(edited by N.Ohkouchi, I. Tayasu, and K. Koba, Enantiomer-specific isotope analysis(ESIA) of D- and L-alanine: nitrogen isotopic hetero- and homogeneity by microbial process and chemical process.) (2010)
  • Author(s): Takano, Y., Chikaraishi, Y., Ohkouchi, N.
  • Publisher: Kyoto University Press.(in press)
• [Book] Earth, Life, and Isotopes (edited by N. Ohkouchi, I. Tayasu, and K. Koba, Instrumental optimization for compound-specific nitrogen isotope analysis of amino acids by gas chromatography/combustion/isotope ratio mass spectrometry.) (2010)
  • Author(s): Chikaraishi Y., Takano Y., Ogawa O.N., Ohkouchi, N.
  • Publisher: Kyoto University Press.(in press)
• [Book] Search and Detection of Life (edited by V. Basiuk, High molecular weight complex organics in interstellar space and their relevance to origins of life. Astrobiology: Emergence) (2010)
  • Author(s): Kobayashi, K., Kaneko, T., Takahashi, J. -I., Takano, Y., Yoshida, S.
  • Total Pages: 175-186
  • Publisher: American Scientific Publishers
• [Book] Organic Matter in Space (edited by S.A. Sandford & S. Kwok, Formation of amino acid precursors with large molecular weight in dense clouds and their relevance to origins of bio-homochirality.) (2008)
  • Author(s): Kobayashi K., Kaneko T., Takano Y., Takahashi J.
  • Total Pages: 465-472
  • Publisher: Cambridge Univ. Press.
• [Remarks]
  • URL: http://www.jamstec.go.jp/biogeos/j/elhrp/biogeochem/