Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold
The synthesis of tripeptides incorporating new fluorinated heterocyclic hydrazino acids, based on the tetrahydropyridazine scaffold is described. Starting from simple fluorinated hydrazones, these non-proteinogenic cyclic β-amino acids were easily prepared by a zinc-catalyzed aza-Barbier reaction fo...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2024-12-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.20.262 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1841557381315559424 |
|---|---|
| author | Thierry Milcent Pascal Retailleau Benoit Crousse Sandrine Ongeri |
| author_facet | Thierry Milcent Pascal Retailleau Benoit Crousse Sandrine Ongeri |
| author_sort | Thierry Milcent |
| collection | DOAJ |
| description | The synthesis of tripeptides incorporating new fluorinated heterocyclic hydrazino acids, based on the tetrahydropyridazine scaffold is described. Starting from simple fluorinated hydrazones, these non-proteinogenic cyclic β-amino acids were easily prepared by a zinc-catalyzed aza-Barbier reaction followed by an intramolecular Michael addition. Preliminary conformational studies on tripeptides including this scaffold in the central position show an extended conformation in solution (NMR) and in the solid state (X-ray). |
| format | Article |
| id | doaj-art-eed6a8ba3177460b90c2fd0d0af3b300 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-eed6a8ba3177460b90c2fd0d0af3b3002025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013174318110.3762/bjoc.20.2621860-5397-20-262Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffoldThierry Milcent0Pascal Retailleau1Benoit Crousse2Sandrine Ongeri3UMR 8076, BioCIS, CNRS, Université Paris-Saclay, avenue des sciences, 91400 Orsay, France Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, 91198 Gif-sur-Yvette, France UMR 8076, BioCIS, CNRS, Université Paris-Saclay, avenue des sciences, 91400 Orsay, France UMR 8076, BioCIS, CNRS, Université Paris-Saclay, avenue des sciences, 91400 Orsay, France The synthesis of tripeptides incorporating new fluorinated heterocyclic hydrazino acids, based on the tetrahydropyridazine scaffold is described. Starting from simple fluorinated hydrazones, these non-proteinogenic cyclic β-amino acids were easily prepared by a zinc-catalyzed aza-Barbier reaction followed by an intramolecular Michael addition. Preliminary conformational studies on tripeptides including this scaffold in the central position show an extended conformation in solution (NMR) and in the solid state (X-ray).https://doi.org/10.3762/bjoc.20.262fluoroalkyl groupsheterocycleshydrazino acidspeptidestetrahydropyridazines |
| spellingShingle | Thierry Milcent Pascal Retailleau Benoit Crousse Sandrine Ongeri Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold Beilstein Journal of Organic Chemistry fluoroalkyl groups heterocycles hydrazino acids peptides tetrahydropyridazines |
| title | Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| title_full | Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| title_fullStr | Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| title_full_unstemmed | Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| title_short | Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| title_sort | synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold |
| topic | fluoroalkyl groups heterocycles hydrazino acids peptides tetrahydropyridazines |
| url | https://doi.org/10.3762/bjoc.20.262 |
| work_keys_str_mv | AT thierrymilcent synthesisofextendedfluorinatedtripeptidesbasedonthetetrahydropyridazinescaffold AT pascalretailleau synthesisofextendedfluorinatedtripeptidesbasedonthetetrahydropyridazinescaffold AT benoitcrousse synthesisofextendedfluorinatedtripeptidesbasedonthetetrahydropyridazinescaffold AT sandrineongeri synthesisofextendedfluorinatedtripeptidesbasedonthetetrahydropyridazinescaffold |