Biomimetic synthetic studies on the hicksoane alkaloids
The hicksoane alkaloids contain an unusual propane-2,2-diamine unit embedded within a 1,3,6-triazocane, the only natural product known to possess this eight-membered heterocycle. Herein, we report the results examining a biosynthesis proposal that this heterocycle emerges from a late-stage reaction...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-03-01
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| Series: | Tetrahedron Chem |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666951X23000268 |
| _version_ | 1797247696517464064 |
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| author | Stephanie Lee Tilo Söhnel Jonathan Sperry |
| author_facet | Stephanie Lee Tilo Söhnel Jonathan Sperry |
| author_sort | Stephanie Lee |
| collection | DOAJ |
| description | The hicksoane alkaloids contain an unusual propane-2,2-diamine unit embedded within a 1,3,6-triazocane, the only natural product known to possess this eight-membered heterocycle. Herein, we report the results examining a biosynthesis proposal that this heterocycle emerges from a late-stage reaction of a dipeptide with acetone. Ile-Trp-CONH2 and Trp-Ile-CONH2 dipeptides were trialled as substrates; in both cases, the intermediate iminium ion did not engage with the primary amide to form the triazocane, reacting instead to generate an imidazolidinone and a β-carboline, respectively. The results from this study infer the triazocane present in these alkaloids is unlikely to be biosynthesised by the late-stage reaction of a dipeptide with biogenic acetone. |
| first_indexed | 2024-03-08T20:10:22Z |
| format | Article |
| id | doaj.art-ac887f5600b24d308d64768ccbd82b37 |
| institution | Directory Open Access Journal |
| issn | 2666-951X |
| language | English |
| last_indexed | 2024-04-24T20:02:48Z |
| publishDate | 2024-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Chem |
| spelling | doaj.art-ac887f5600b24d308d64768ccbd82b372024-03-24T07:02:05ZengElsevierTetrahedron Chem2666-951X2024-03-019100060Biomimetic synthetic studies on the hicksoane alkaloidsStephanie Lee0Tilo Söhnel1Jonathan Sperry2School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New ZealandSchool of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New ZealandCorresponding author.; School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New ZealandThe hicksoane alkaloids contain an unusual propane-2,2-diamine unit embedded within a 1,3,6-triazocane, the only natural product known to possess this eight-membered heterocycle. Herein, we report the results examining a biosynthesis proposal that this heterocycle emerges from a late-stage reaction of a dipeptide with acetone. Ile-Trp-CONH2 and Trp-Ile-CONH2 dipeptides were trialled as substrates; in both cases, the intermediate iminium ion did not engage with the primary amide to form the triazocane, reacting instead to generate an imidazolidinone and a β-carboline, respectively. The results from this study infer the triazocane present in these alkaloids is unlikely to be biosynthesised by the late-stage reaction of a dipeptide with biogenic acetone.http://www.sciencedirect.com/science/article/pii/S2666951X23000268 |
| spellingShingle | Stephanie Lee Tilo Söhnel Jonathan Sperry Biomimetic synthetic studies on the hicksoane alkaloids Tetrahedron Chem |
| title | Biomimetic synthetic studies on the hicksoane alkaloids |
| title_full | Biomimetic synthetic studies on the hicksoane alkaloids |
| title_fullStr | Biomimetic synthetic studies on the hicksoane alkaloids |
| title_full_unstemmed | Biomimetic synthetic studies on the hicksoane alkaloids |
| title_short | Biomimetic synthetic studies on the hicksoane alkaloids |
| title_sort | biomimetic synthetic studies on the hicksoane alkaloids |
| url | http://www.sciencedirect.com/science/article/pii/S2666951X23000268 |
| work_keys_str_mv | AT stephanielee biomimeticsyntheticstudiesonthehicksoanealkaloids AT tilosohnel biomimeticsyntheticstudiesonthehicksoanealkaloids AT jonathansperry biomimeticsyntheticstudiesonthehicksoanealkaloids |