Computational study on formation of 15-membered azalactone by double reductive amination using molecular mechanics and density functional theory calculations
Formation of 15-membered azalactone by double reductive amination was analyzed using molecular mechanics and density functional theory calculations for simplified model compounds. As a result, the following aspects were clarified. When methylamine attacks a linear bis-aldehyde in the first step, the...
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| Veröffentlicht in: | Journal of antibiotics 2018-05, Vol.71 (5), p.549-556 |
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| container_title | Journal of antibiotics |
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| creator | Gouda, Hiroaki Nakayama, Naofumi Miura, Tomoaki Kanemoto, Kenichi Ajito, Keiichi |
| description | Formation of 15-membered azalactone by double reductive amination was analyzed using molecular mechanics and density functional theory calculations for simplified model compounds. As a result, the following aspects were clarified. When methylamine attacks a linear bis-aldehyde in the first step, there are possibilities that two regioisomers are formed. However, one of them exhibited remarkably stable energy level compared with the other. The stable isomer indicated a short distance between a methylamine moiety and an unreacted aldehyde. This short distance, about 2.3 Å, could be explained by hydrogen bonding, which implied relatively easy cyclization in the second step. Moreover, this cyclization process was supposed to be exothermic according to comparison of energy levels before and after cyclization. |
| doi_str_mv | 10.1038/s41429-018-0030-6 |
| format | Article |
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As a result, the following aspects were clarified. When methylamine attacks a linear bis-aldehyde in the first step, there are possibilities that two regioisomers are formed. However, one of them exhibited remarkably stable energy level compared with the other. The stable isomer indicated a short distance between a methylamine moiety and an unreacted aldehyde. This short distance, about 2.3 Å, could be explained by hydrogen bonding, which implied relatively easy cyclization in the second step. 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As a result, the following aspects were clarified. When methylamine attacks a linear bis-aldehyde in the first step, there are possibilities that two regioisomers are formed. However, one of them exhibited remarkably stable energy level compared with the other. The stable isomer indicated a short distance between a methylamine moiety and an unreacted aldehyde. This short distance, about 2.3 Å, could be explained by hydrogen bonding, which implied relatively easy cyclization in the second step. 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As a result, the following aspects were clarified. When methylamine attacks a linear bis-aldehyde in the first step, there are possibilities that two regioisomers are formed. However, one of them exhibited remarkably stable energy level compared with the other. The stable isomer indicated a short distance between a methylamine moiety and an unreacted aldehyde. This short distance, about 2.3 Å, could be explained by hydrogen bonding, which implied relatively easy cyclization in the second step. Moreover, this cyclization process was supposed to be exothermic according to comparison of energy levels before and after cyclization.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>29515229</pmid><doi>10.1038/s41429-018-0030-6</doi><tpages>8</tpages></addata></record> |
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| subjects | 631/326/22/1290 631/92/606 Aldehydes Amination Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Brief Communication Computational Biology Cyclization Density Functional Theory Hydrogen Bonding Lactones - chemical synthesis Life Sciences Medicinal Chemistry Microbiology Models, Molecular Organic Chemistry Stereoisomerism |
| title | Computational study on formation of 15-membered azalactone by double reductive amination using molecular mechanics and density functional theory calculations |
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