0000000001314862
AUTHOR
Julie Bernard
showing 9 related works from this author
Phosphonium-Boronate Amino Acid Derivatives as Fluoride Pincers for 18F-Labelling
2015
The synthesis of phosphonium-boronate amino acid derivatives was achieved by quaternization of o-boronatophenylphosphine with iodo-amino acid derivatives. Preliminary radiolabelling studies demonst...
o-BF3-Phosphonium pincer moieties in the design of delocalized lipophilic cation based tracers for PET imaging of mitochondrial function
2017
International audience; Objectives: Delocalized lipophilic cations, such as triphenylphosphonium (TPP), are able to cross cell membranes and are known to accumulate in the mitochondria in a membrane potential (MMP) dependent manner. MMP is a reliable indicator of mitochondrial and, consequently, cell and tissue function, hence MMP dependent uptake radiotracers are of interest in cardiac and tumour imaging. Conventional C-18F radiofluorination methods require strict aprotic conditions and heating, moreover, C-18F fluorinated tracers may suffer from metabolic defluorination reducing the quality of the images. The objective of this study was to investigate a suitability of o-B[18F]F3-phosphoni…
o-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
2015
The synthesis of o-boronato- and o-trifluoroborato-phosphonium salts supported by the L-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from L-serine or L-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato-phosphonium amino esters, respectively. The usefulness of these compounds in peptide cou…
Efficient Synthesis of (P-Chirogenic) o-Boronated Phosphines from sec-Phosphine Boranes
2015
An efficient synthesis of boronated phosphines with an o-phenylene-bridge prepared from sec-phosphine boranes and using benzyne chemistry is reported. Successive reactions of sec-phosphine boranes with n-BuLi and 1,2-dibromobenzene, and then with boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use of P-chirogenic sec-phosphine boranes leads to the free boronated phosphines with retention of configuration at the P-center after decomplexation. The reaction of P-chirogenic o-boronatophenylphosphine with KHF2 affords the corresponding trifluoroborated phosphine with ee >98%.
ChemInform Abstract: O-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
2015
The synthesis of o-boronato- and o-trifluoroborato–phosphonium salts supported by the l-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from l-serine or l-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato–phosphonium amino esters, respectively. The usefulness of these compounds in peptide cou…
Synthèse de pinces à fluorures dérivées d'aminoacides pour l'imagerie TEP
2014
This thesis project, which is part of a collaboration between the Institut de Chimie Moléculaire de l’Université de Bourgogne and the Positron Emission Tomography Research Centre, is about the synthesis of fluoride pincers derived from amino acids based on 18F-B bond construction to get a new class of PET imaging agents. First, this project concerned the design, synthesis and characterisation of new boronato and trifluoroborato phosphonium amino acid salts. Quaternisation of o-boronate phenyl phosphine with β-iodo amino esters or γ-iodo amino ester leads to the corresponding salts without racemisation and in yields up to 88%. Saponification of boronato phosphonium amino esters afford the fr…
CCDC 1053706: Experimental Crystal Structure Determination
2015
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167
CCDC 1053707: Experimental Crystal Structure Determination
2015
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167
CCDC 1053708: Experimental Crystal Structure Determination
2015
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167