Total Synthesis of Cyclosenegalin A
Abstract A Pro‐Gly‐typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid‐ and solution‐phase synthetic methods. This study also compared the effectiveness of β...
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Wiley-VCH
2024-12-01
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| Online Access: | https://doi.org/10.1002/open.202400175 |
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| author | Anderson Arnold Aloanis Prof. Tati Herlina Dr. Ari Hardianto Prof. Rani Maharani |
| author_facet | Anderson Arnold Aloanis Prof. Tati Herlina Dr. Ari Hardianto Prof. Rani Maharani |
| author_sort | Anderson Arnold Aloanis |
| collection | DOAJ |
| description | Abstract A Pro‐Gly‐typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid‐ and solution‐phase synthetic methods. This study also compared the effectiveness of β‐turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β‐turn type I inducer (Ser‐Ala‐Val‐Thr) as turning point and second sequence employed β‐turn type II inducer (Thr‐Pro‐Gly‐Leu). The successful cyclization was obtained using the linear sequence of NH2‐Ala‐Val‐Thr‐Pro‐Gly‐Leu‐Ser‐OH with β‐turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR‐ToFMS, 1H NMR, 13C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity. |
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| issn | 2191-1363 |
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| publishDate | 2024-12-01 |
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| spelling | doaj-art-78988d367a0a4ccb89a90b85e85ee5aa2025-08-20T02:20:51ZengWiley-VCHChemistryOpen2191-13632024-12-011312n/an/a10.1002/open.202400175Total Synthesis of Cyclosenegalin AAnderson Arnold Aloanis0Prof. Tati Herlina1Dr. Ari Hardianto2Prof. Rani Maharani3Department Chemistry Universitas Negeri Manado Minahasa 95619Department Chemistry Universitas Padjadjaran Jatinangor 45363Department Chemistry Universitas Padjadjaran Jatinangor 45363Department Chemistry Universitas Padjadjaran Jatinangor 45363Abstract A Pro‐Gly‐typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid‐ and solution‐phase synthetic methods. This study also compared the effectiveness of β‐turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β‐turn type I inducer (Ser‐Ala‐Val‐Thr) as turning point and second sequence employed β‐turn type II inducer (Thr‐Pro‐Gly‐Leu). The successful cyclization was obtained using the linear sequence of NH2‐Ala‐Val‐Thr‐Pro‐Gly‐Leu‐Ser‐OH with β‐turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR‐ToFMS, 1H NMR, 13C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity.https://doi.org/10.1002/open.202400175Beta-turnCyclopeptideSolid-phase synthesisSolution-phase synthesisTotal synthesis |
| spellingShingle | Anderson Arnold Aloanis Prof. Tati Herlina Dr. Ari Hardianto Prof. Rani Maharani Total Synthesis of Cyclosenegalin A ChemistryOpen Beta-turn Cyclopeptide Solid-phase synthesis Solution-phase synthesis Total synthesis |
| title | Total Synthesis of Cyclosenegalin A |
| title_full | Total Synthesis of Cyclosenegalin A |
| title_fullStr | Total Synthesis of Cyclosenegalin A |
| title_full_unstemmed | Total Synthesis of Cyclosenegalin A |
| title_short | Total Synthesis of Cyclosenegalin A |
| title_sort | total synthesis of cyclosenegalin a |
| topic | Beta-turn Cyclopeptide Solid-phase synthesis Solution-phase synthesis Total synthesis |
| url | https://doi.org/10.1002/open.202400175 |
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