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Metabolites 2018, 8(3), 48; https://doi.org/10.3390/metabo8030048

The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis

1
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan
2
Cluster of Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
3
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
4
RIKEN Center for Sustainable Resource Science (Yokohama campus), 1-7-22 Suehiro-cho, Tsurumi-ku, Yokohama 230-0045, Japan
*
Author to whom correspondence should be addressed.
Received: 24 July 2018 / Revised: 30 August 2018 / Accepted: 30 August 2018 / Published: 31 August 2018
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Abstract

Lys-derived alkaloids widely distributed in plant kingdom have received considerable attention and have been intensively studied; however, little is known about their biosynthetic mechanisms. In terms of the skeleton formation, for example, of quinolizidine alkaloid biosynthesis, only the very first two steps have been identified and the later steps remain unknown. In addition, there is no available information on the number of enzymes and reactions required for their skeletal construction. The involvement of the Δ 1 -piperideine dimerization has been proposed for some of the Lys-derived alkaloid biosyntheses, but no enzymes for this dimerization reaction have been reported to date; moreover, it is not clear whether this dimerization reaction proceeds spontaneously or enzymatically. In this study, the energetic viability of the Δ 1 -piperideine dimerizations under neutral and acidic conditions was assessed using the density functional theory computations. In addition, a similar type of reaction in the dipiperidine indole alkaloid, nitramidine, biosynthesis was also investigated. Our findings will be useful to narrow down the candidate genes involved in the Lys-derived alkaloid biosynthesis. View Full-Text
Keywords: alkaloid; quinolizidine; lysine; plant; piperideine; nitramidine; DFT calculation alkaloid; quinolizidine; lysine; plant; piperideine; nitramidine; DFT calculation
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Sato, H.; Uchiyama, M.; Saito, K.; Yamazaki, M. The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis. Metabolites 2018, 8, 48.

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