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Molecular Evolution of N-Containing Cyclic Compounds in the Parent Body of the Murchison Meteorite
ACS Earth and Space Chemistry ( IF 3.4 ) Pub Date : 2017-10-02 00:00:00 , DOI: 10.1021/acsearthspacechem.7b00058
Hiroshi Naraoka , Yohei Yamashita , Mihoko Yamaguchi 1 , François-Régis Orthous-Daunay 2
Affiliation  

Primitive meteorites contain various classes of organic compounds. Because the molecular distribution in these meteorites is not fully clarified, we do not yet understand the comprehensive formation mechanism(s) of extraterrestrial organic compounds. In this study, diverse and abundant alkylated homologues of N-containing cyclic compounds were identified in the methanol extract of the Murchison meteorite by electrospray ionization using high-performance liquid chromatography/ultrahigh-resolution mass spectrometry. More than 600 positive ions were assigned to CnHmN+ and CnHmN2+, in which saturated and unsaturated alkylated pyridines and alkylimidazoles are predominant. Both can be synthesized from aldehydes and ammonia through aldol condensation and imine formation under an alkaline environment. Further redox reactions could have proceeded to make these molecules evolve to various CHN compounds, including alkylpiperidines and pyridine carboxylic acids. This study indicates that aldol condensation and formose reaction with ammonia are an important mechanism for the molecular evolution of N-containing compounds in the asteroid.

中文翻译:

默奇森陨石母体中含氮环状化合物的分子演化

原始陨石包含各种类别的有机化合物。由于尚未完全弄清这些陨石中的分子分布,因此我们尚不了解地球外有机化合物的综合形成机理。在这项研究中,使用高效液相色谱/超高分辨率质谱通过电喷雾电离在Murchison陨石的甲醇提取物中鉴定出了多种多样且丰富的含N环状化合物的烷基化同系物。超过600个正离子分配给C n H m N +和C n H m N 2 +,其中主要是饱和和不饱和烷基化吡啶和烷基咪唑。两者均可在碱性环境下由醛和氨通过醛醇缩合和亚胺形成而合成。可能已经进行了进一步的氧化还原反应,使这些分子演化为各种CHN化合物,包括烷基哌啶和吡啶羧酸。这项研究表明,羟醛缩合和与氨的甲酸酯反应是小行星中含氮化合物分子进化的重要机制。
更新日期:2017-10-02
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