Artificial Dnazyme for Asymmetric Oxidations
Il y a 2 mois
**Artificial DNAzyme for asymmetric oxidations**:
- Réf **ABG-121895**
- Sujet de Thèse- 27/03/2024- Contrat doctoral- Département de Chimie Moléculaire- Lieu de travail- Grenoble - Auvergne-Rhône-Alpes - France- Intitulé du sujet- Artificial DNAzyme for asymmetric oxidations- Champs scientifiques- Chimie
- Mots clés- Bioorganic chemistry, Asymmetric catalysis, Conjugation.**Description du sujet**:
- The use of nucleic acids as chiral auxiliaries represents an interesting alternative. They can be produced chemically, and while the three-dimensional structures they form (eg. duplexes) are also sensitive to denaturation, this is reversible. The use of double-stranded DNA for various asymmetric transformations has been shown to be possible.3-6 The use of G4-quadruplex (G4) structures,7 based on the stacking of guanine tetrads for asymmetric catalysis, has recently attracted interest.8-11 One of the feature of these structures is that a single DNA sequence can adopt several G4 topologies (conformations) that are in equilibrium with each other.- In asymmetric catalysis, these different topologies lead to different efficiencies and orientations,12 demonstrating that controlling the conformation of G4 is crucial. This can be achieved by immobilizing guanine-rich oligonucleotides on a peptide template to create mimics of a specific G4 topology.13,14- We have shown that these mimes can catalyze the enantioselective oxidation of thioethers in combination with a copper II complex.15 However, this enantioselective transformation competes with racemic sulfoxidation, which occurs outside G4. In addition, the enantiomer obtained depends mainly on the G4 region where the reaction occurs.The thesis project aims to overcome these limitations by conjugating the metal complex to a precise region of the G4 mime. This strategy should make it possible to (i) prevent the reaction from occurring outside G4, (ii) control the orientation of the reaction by controlling the site where it takes place, and (iii) open up other enantioselective oxidation transformations such as olefin epoxidation.
The PhD student's tasks will be to synthesize modified G4s at the Department of Molecular Chemistry (DCM), characterize them and test them in asymmetric oxidation catalysis, in collaboration with the Laboratory of Metals Chemistry and Biology (LCBM).
**Bibliography**:
1 C. A. Busacca, D. R. Fandrick, J. J. Song and C. H. Senanayake, _Adv. Synth. Catal._, 2011, **353**, 1825-1864.
2 J.M. Choi, S.S. Han and H.S. Kim, _Biotechnol. Adv._, 2015, **33**, 1443-1454.
3 G. Roelfes and B. L. Feringa, _Angew. Chem. Int. Ed._, 2005, **44**, 3230-3232.
4 D. Coquière, B. L. Feringa and G. Roelfes, _Angew. Chem. Int. Ed._, 2007, **46**, 9308-9311.
5 A. Rioz-Martínez, J. Oelerich, N. Ségaud and G. Roelfes, _Angew. Chem. Int. Ed._, 2016, **55**, 14136-14140.
6 A. J. Boersma, B. L. Feringa and G. Roelfes, _Angew. Chem. Int. Ed._, 2009, **48**, 3346-3348.
7 S. Burge, G. N. Parkinson, P. Hazel, A. K. Todd and S. Neidle, _Nucleic Acids Res._, 2006, **34**, 5402-5415.
8 S. Roe, D. J. Ritson, T. Garner, M. Searle and J. E. Moses, _Chem. Commun._, 2010, **46**, 4309-4311.
9 L.X. Wang, J.F. Xiang and Y.L. Tang, _Adv. Synth. Catal._, 2015, **357**, 13-20.
10 J. H. Yum, S. Park and H. Sugiyama, _Org. Biomol. Chem._, 2019, **17**, 9547-9561.
11 M. Cheng, Y. Li, J. Zhou, G. Jia, S.M. Lu, Y. Yang and C. Li, _Chem. Commun._, 2016, **52**, 9644-9647.
12 C. Wang, G. Jia, Y. Li, S. Zhang and C. Li, _Chem. Commun._, 2013, **49**, 11161-11163.
13 P. Murat, D. Cressend, N. Spinelli, A. Van der Heyden, P. Labbe, P. Dumy and E. Defrancq, _ChemBioChem_, 2008, **9**, 2588-2591.
14 R. Bonnet, T. Lavergne, B. Gennaro, N. Spinelli and E. Defrancq, _Chem. _Commun._, 2015, **51**, 4850-3.
15 Y. Colas, S. Ménage, C. Marchi-Delapierre and N. Spinelli, _ChemCatChem_, 2023, **n/a**, e202300914.
**Prise de fonction**:
- 01/10/2024**Nature du financement**:
- Contrat doctoral**Précisions sur le financement**:
- Graduate School (EUR) CBH- Chemistry, Biology and Health**Présentation établissement et labo d'accueil**:
- Département de Chimie MoléculaireLe Département de Chimie Moléculaire de Grenoble est une unité mixte de recherche (UMR 5250) associant le CNRS et l’Université Grenoble Alpes. Le DCM a été créé le 01 Janvier 2007 suite à la fusion du Laboratoire d’Électrochimie Organique et de Photochimie Redox (LEOPR, UMR 5630) et du Laboratoire d’Études Dynamiques et Structurales de la Sélectivité (LEDSS, UMR 5616). A ce jour, le DCM mobilise environ 150 personnes dont les orientations scientifiques sont tournées vers les grands thèmes sociétaux : santé et bien-être, et nouvelles énergies, sans oublier les aspects fondamentaux.
Ces équipes de recherches disposent d’un solide soutien technique:
- Institut de Chimie Moléculaire de Grenoble ICMG
- Plateforme Physico-Chimie
- Plateforme Synthèse
- Informatique
Le DCM bénéficie de p
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