N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis
| العنوان: | N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis |
|---|---|
| المؤلفون: | Kelly Maurent, Aurélien Lebrun, Emmanuel Aubert, Jean Martinez, Monique Calmes, Claude Didierjean, Pierre Milbeo, Laure Moulat |
| المساهمون: | Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Cristallographie, Résonance Magnétique et Modélisations (CRM2), Centre National de la Recherche Scientifique (CNRS)-Université de Lorraine (UL) |
| المصدر: | Tetrahedron Tetrahedron, Elsevier, 2016, 72 (13), pp.1706-1715. ⟨10.1016/j.tet.2016.02.027⟩ |
| بيانات النشر: | HAL CCSD, 2016. |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Asymmetric aldol reaction, Bicyclic molecule, 010405 organic chemistry, Stereochemistry, Organocatalysis, Carboxylic acid, Organic Chemistry, Absolute configuration, Tripeptide, 010402 general chemistry, 01 natural sciences, Biochemistry, Pyrrolidine, Short alpha/beta-peptide, 0104 chemical sciences, chemistry.chemical_compound, Residue (chemistry), chemistry, Aldol reaction, Drug Discovery, [CHIM.CRIS]Chemical Sciences/Cristallography, Bicyclic beta-amino acid |
| الوصف: | International audience; A series of N-pyrrolidine-based alpha,beta-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2] octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording beta-hydroxy ketones in high yields and good enantioselectivities (up to 87%). |
| اللغة: | English |
| تدمد: | 0040-4020 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3144848b1e1121981a3275fff34a723e https://hal.univ-lorraine.fr/hal-01532027 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi.dedup.....3144848b1e1121981a3275fff34a723e |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 00404020 |
|---|