CAVELIER Florine
Team: Synthèses Stéréosélectives & Acides Aminés Modifiés
florine.cavelier
umontpellier.fr
0448792134
Room: N3H15 - Site : Pôle Chimie Balard Recherche
Research Topics: - chim
- chim/chim.cris
- chim/chim.orga
- sdv/sdv.bbm/sdv.bbm.bm
- sdv/sdv.bbm/sdv.bbm.bs
- sdv/sdv.bbm/sdv.bbm.bc
- sdv/sdv.bbm/sdv.bbm.gtp
- sdv/sdv.bv
- chim/chim.theo
- sdv/sdv.sa
- sdv/sdv.can
- sdv/sdv.sp
- sdv/sdv.bbm
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Last scientific productions :
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Phospholyl(borane) Amino Acids and Peptides: Stereoselective Synthesis and Fluorescent Properties with Large Stokes Shift
Author(s): Arribat M., Remond E., Clément Sébastien, Lee Arie van der, Cavelier F.
(Article) Published:
Journal Of The American Chemical Society, vol. 140 p.1028 - 1034 (2018)
Ref HAL: hal-01708759_v1
PMID 29262677
DOI: 10.1021/jacs.7b10954
Abstract: The synthesis of phospholyl(borane) amino acids was stereoselectively achieved by reaction of phospholide anion with iodo α-amino ester derived from l-aspartic acid or l-serine, followed by in situ complexation with borane. Phospholyl(borane) amino acids are easy to store and can be subjected to direct transformation into the corresponding free phospholyl, gold complex, oxide or sulfur derivatives as well as phospholinium salts, thus offering a variety of side chains. After selective deprotection of carboxylic function or amine, C- or N- peptide coupling with an alanine moiety proved the possible incorporation into peptides. Such phospholyl amino acid and peptide derivatives exhibit fluorescent properties with a large Stokes shift (160 nm) and fluorescence up to 535 nm, depending on the phosphole aromaticity and the chemical environment. These phospholyl(borane) amino acids constitute a new class of unnatural amino acids useful for structure–activities relationship studies and appear to be promising fluorophores for the development of labeled peptides.
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Hydrophobic alpha,alpha-Disubstituted Disilylated TESDpg Induces Incipient 3 10 -Helix in Short Tripeptide Sequence
Author(s): Fanelli R., Berthomieu Dorothée, Didierjean Claude, Doudouh Abdelatif, Lebrun A., Martinez J., Cavelier F.
(Article) Published:
Organic Letters, vol. 19 p.2937 - 2940 (2017)
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First identification and quantification of S-3-(hexan-1-ol)-gamma-glutamyl-cysteine in grape must as a potential thiol precursor, using UPLC-MS/MS analysis and stable isotope dilution assay
Author(s): Bonnaffoux Hugo, Roland Aurélie, Remond E., Delpech Stéphanie, Schneider Remi, Cavelier F.
(Article) Published:
Food Chemistry, vol. 237 p.877-886 (2017)
Ref HAL: hal-01837818_v1
PMID 28764081
DOI: 10.1016/j.foodchem.2017.05.116
Abstract: Varietal thiols are key aroma compounds in wine issued from multiple and complex origins. Several precursor families have been identified in grapes and must and have been widely studied. But a large part of thiol origin still remains unknown. Thus, we only have an incomplete picture of thiol precursors and there is a lack of knowledge on pre-fermentative mechanisms that can impact their levels. Our study focused on the formal identification and the quantification of new varietal thiol precursors in must. First of all, we synthesized natural and labeled standards using an original multi-step strategy, then we developed and validated a UPLC-MS/MS method that allowed us to identify and quantify for the first time a dipeptide S-conjugate to 3MH, the gamma GluCys-3MH, in Sauvignon B. We observed the S-4-mercapto-4-methylpentan-2-one-L-cysteinyl-glycine (CysGly-4MMP) and S-4-mercapto-4-methylpentan-2-one-N-(L-gamma-glutamyl)-L-cysteine (gamma GluCys-4MMP) but at too low concentration to be quantified.
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Prediction of pKa Using DFT: the Nicotianamine Polyacid Example
Author(s): Giard Aude, Filhol J.-S., Jolibois Franck, Cavelier F., Berthomieu Dorothée
(Article) Published:
Journal Of Chemical Theory And Computation, vol. 12 p.5493 (2016)
Ref HAL: hal-01412041_v1
DOI: 10.1021/acs.jctc.6b00404
Abstract: The determination of pKa values for molecules containing multiple acidic groups in solution is challenging both experimentally and theoretically. We propose a general method to obtain these values by combining a graphical analysis based on a predominance diagram, for amino acids and nicotianamine polyacid, with first principle DFT calculations. Implicit and semiexplicit water solvent models were included to account for solvation. This strategy enables the investigation of the protonation states of compounds containing acidic moieties in solution depending on the pH domain. The method was first validated on a set of amino acids with pKa values calculated with an accuracy within 0.5–1.0 pKa unit and then on the chalenging nicotianamine polyacid with six pKa values. This approach is particularly well suited for such a complex system including both zwitterionic structures and unknown experimental pKa values.
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Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis
Author(s): Cavelier F.
(Article) Published:
Organic Letters, vol. 17 p. (2015)
Ref HAL: hal-01212249_v1
DOI: 10.1021/acs.orglett.5b02175
Abstract: A concise synthetic pathway yielding to hydrophobic α,α-disubstituted disilylated amino acids based on a hydrosilylation reaction is described. As a first example of utilization in solid-phase peptide synthesis, TESDpg was introduced in replacement of Aib in an alamethicin sequence, leading to analogues with modified physicochemical properties and conserved helical structures. This study highlights the potential of these new amino acids as tools for peptide modulation.
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