Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C
Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These molecules present a ?-hydroxyoctanoic acid coupled to well-defined amino acid or ?-hydroxy acid residue sequences and have been isolated from the marine cyanobacteria Okeania sp. in Japan, 2017.1 Kohamamid...
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| Formato: | Online |
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Universidade Estadual de Campinas
2019
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| Acceso en línea: | https://econtents.sbu.unicamp.br/eventos/index.php/pibic/article/view/470 |
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| author | Silva, Gabriel Aparecido Miranda e Pastre, Julio Cezar Novaes, Luiz F. T. Henrique, Christian Leonardo |
| author_facet | Silva, Gabriel Aparecido Miranda e Pastre, Julio Cezar Novaes, Luiz F. T. Henrique, Christian Leonardo |
| author_sort | Silva, Gabriel Aparecido Miranda e |
| collection | Portal de Eventos Científicos da UNICAMP |
| container_reference | Revista dos Trabalhos de Iniciação Científica da UNICAMP; n. 26 (2018): Congresso de Iniciação Científica Unicamp |
| description | Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These molecules present a ?-hydroxyoctanoic acid coupled to well-defined amino acid or ?-hydroxy acid residue sequences and have been isolated from the marine cyanobacteria Okeania sp. in Japan, 2017.1 Kohamamides chemical structures were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry analyses. Isolated kohamamides showed pronounced cytotoxic activity against cell lines of human leukemia, being kohamamide B the most active (IC50 = 6.0 µM). In this context, we propose the first total syntheses of Kohamamides A, B e C, in a total of 15 steps. The synthetic retro analysis consisted in the fragmentation of main blocks, 4 and 5. Initially, the intermediates 2 and 3 were obtained with high yield (2, 79% for 2 steps, and 3 with quantitative yield) and the synthesis of fragment 11 in good yield (68%). Additional efforts will be directed to the synthesis of intermediate 1, followed by the coupling of 1, 2 and 11 to form fragment 4. Finally, the synthesis of 5 and coupling between the key intermediates 4 and 5 will furnish the desired natural products Kohamamides A, B and C. With the final compounds in hands, in vitro cytotoxicity evaluation will be conducted. |
| first_indexed | 2025-10-08T13:50:56Z |
| format | Online |
| id | ojs-article-470 |
| institution | Universidade Estadual de Campinas |
| issn | 2596-1969 |
| language | eng |
| last_indexed | 2025-10-08T13:50:56Z |
| publishDate | 2019 |
| publisher | Universidade Estadual de Campinas |
| record_format | ojs |
| spelling | ojs-article-4702025-09-26T14:32:30Z Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C Silva, Gabriel Aparecido Miranda e Pastre, Julio Cezar Novaes, Luiz F. T. Henrique, Christian Leonardo Natural product Cyclic depsipeptides Total synthesis. Kohamamides A, B and C are cyclic depsipeptides that belong to the kulolide superfamily. These molecules present a ?-hydroxyoctanoic acid coupled to well-defined amino acid or ?-hydroxy acid residue sequences and have been isolated from the marine cyanobacteria Okeania sp. in Japan, 2017.1 Kohamamides chemical structures were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry analyses. Isolated kohamamides showed pronounced cytotoxic activity against cell lines of human leukemia, being kohamamide B the most active (IC50 = 6.0 µM). In this context, we propose the first total syntheses of Kohamamides A, B e C, in a total of 15 steps. The synthetic retro analysis consisted in the fragmentation of main blocks, 4 and 5. Initially, the intermediates 2 and 3 were obtained with high yield (2, 79% for 2 steps, and 3 with quantitative yield) and the synthesis of fragment 11 in good yield (68%). Additional efforts will be directed to the synthesis of intermediate 1, followed by the coupling of 1, 2 and 11 to form fragment 4. Finally, the synthesis of 5 and coupling between the key intermediates 4 and 5 will furnish the desired natural products Kohamamides A, B and C. With the final compounds in hands, in vitro cytotoxicity evaluation will be conducted. Universidade Estadual de Campinas 2019-01-04 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Artigo de convidado application/pdf https://econtents.sbu.unicamp.br/eventos/index.php/pibic/article/view/470 10.20396/revpibic262018470 Revista dos Trabalhos de Iniciação Científica da UNICAMP; n. 26 (2018): Congresso de Iniciação Científica Unicamp 2596-1969 eng https://econtents.sbu.unicamp.br/eventos/index.php/pibic/article/view/470/441 Copyright (c) 2019 Gabriel Aparecido Miranda e Silva, Julio Cezar Pastre http://creativecommons.org/licenses/by/4.0 |
| spellingShingle | Silva, Gabriel Aparecido Miranda e Pastre, Julio Cezar Novaes, Luiz F. T. Henrique, Christian Leonardo Natural product Cyclic depsipeptides Total synthesis. Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title | Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title_full | Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title_fullStr | Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title_full_unstemmed | Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title_short | Towards the synthesis of cyclic depsipeptides Kohamamides A, B and C |
| title_sort | towards the synthesis of cyclic depsipeptides kohamamides a, b and c |
| topic | Natural product Cyclic depsipeptides Total synthesis. |
| url | https://econtents.sbu.unicamp.br/eventos/index.php/pibic/article/view/470 |
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