The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis
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...
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MDPI AG
2018-08-01
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| Series: | Metabolites |
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| Online Access: | http://www.mdpi.com/2218-1989/8/3/48 |
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| author | Hajime Sato Masanobu Uchiyama Kazuki Saito Mami Yamazaki |
| author_facet | Hajime Sato Masanobu Uchiyama Kazuki Saito Mami Yamazaki |
| author_sort | Hajime Sato |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-10T15:07:29Z |
| format | Article |
| id | doaj.art-347a07382098445fbd5c7fa5795e371e |
| institution | Directory Open Access Journal |
| issn | 2218-1989 |
| language | English |
| last_indexed | 2024-12-10T15:07:29Z |
| publishDate | 2018-08-01 |
| publisher | MDPI AG |
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| series | Metabolites |
| spelling | doaj.art-347a07382098445fbd5c7fa5795e371e2022-12-22T01:44:00ZengMDPI AGMetabolites2218-19892018-08-01834810.3390/metabo8030048metabo8030048The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid BiosynthesisHajime Sato0Masanobu Uchiyama1Kazuki Saito2Mami Yamazaki3Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, JapanCluster of Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, JapanGraduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, JapanGraduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, JapanLys-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.http://www.mdpi.com/2218-1989/8/3/48alkaloidquinolizidinelysineplantpiperideinenitramidineDFT calculation |
| spellingShingle | Hajime Sato Masanobu Uchiyama Kazuki Saito Mami Yamazaki The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis Metabolites alkaloid quinolizidine lysine plant piperideine nitramidine DFT calculation |
| title | The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis |
| title_full | The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis |
| title_fullStr | The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis |
| title_full_unstemmed | The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis |
| title_short | The Energetic Viability of Δ1-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis |
| title_sort | energetic viability of δ1 piperideine dimerization in lysine derived alkaloid biosynthesis |
| topic | alkaloid quinolizidine lysine plant piperideine nitramidine DFT calculation |
| url | http://www.mdpi.com/2218-1989/8/3/48 |
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