L'épreuve orale de sciences et technologie au CRPE. Paris : Ellipses

International audienc

L'épreuve orale de sciences et technologie au CRPE. Paris : Ellipses

International audienc

L'épreuve orale de sciences et technologie au CRPE. Paris : Ellipses

International audienc

6-Aminopenicillanic acid (6-APA) derivatives equipped with anchoring arms

6-APA derivatives were considered as selective labels for the construction of bifunctional linkers dedicated to the oriented immobilization of proteins on materials. Sulbactam-like compounds (i.e., 6-β-sulfonamido-penam sulfones) and penicillin G - like compounds (i.e., para-substituted 6-β- phenylacetamido-penams) were prepared and tested as irreversible inhibitors of representative β-lactamases and D,D-peptidases, respectively. The activity of the modified antibiotics was preserved despite their substitution with various anchoring arms. The (2-nitro-4,5-dimethoxy)-benzyl esters revealed of particular interest due to their capacity to acylate BlaR-CTD without deprotection. © 2012 Elsevier Ltd. All rights reserved

Synthesis and characterization of aromatic self-assembled monolayers containing methylene and ethyleneglycol entities by means of sum-frequency generation spectroscopy

We use infrared-visible sum-frequency generation (SFG) spectroscopy in order to investigate the adsorption properties on Pt(111) of molecules having CH3–C6H4–(O–CH2–CH2)n –O–(CH2)m –SH as general chemical formula. We synthesized three molecules defined by the values m=5 n =4, m =11 n =4, m=11 n =8 and characterized them by Nuclear Magnetic Resonance spectroscopy. Thanks to spectroscopic measurements, we show that these molecules build self-assembled monolayers on Pt(111). First, the weak SFG signals arising from the ad-layer indicate low order and surface coverage of the substrate by these molecules. Next, the vibrational fingerprints of the aforementioned molecules are determined between 2825 and 3125 cm 1 and the observed SFG spectral features are ascribed on the basis of the analysis of shorter and simpler molecules (1- dodecanethiol, 4-methylbenzenethiol and CH3–C6H4–O–(CH2)11–SH) also adsorbed on Pt(111). The occurrence of methylene vibration modes indicates a significant amount of chain defects whatever the n and m numbers are. Finally, the identification of a particular vibration mode, characteristic of the aromatic ring, enables us to qualitatively discuss the effect of the number of methylene and ethylene glycol entities on its orientation. More precisely, higher these numbers, more tilted (with respect to the substrate normal) the aromatic ring plane is

Comparative study of decyl thiocyanate and decanethiol self-assembled monolayers on gold substrates

In a recent paper Ciszek et al. [J.W. Ciszek, M.P. Stewart, J.M. Tour, J. Am. Chem. Soc. 126 2004) 13172] showed that organic thiocyanates may be an interesting alternative to the use of thiols for thiolate assemblies. We use scanning tunnelling microscopy (STM), infrared reflection absorption and sum-frequency generation spectroscopies (IRRAS and SFG) in order to study the adsorption properties of decyl thiocyanates (DTCN) and compare them to the decanethiol (DT) ones. Firstly, IRRAS measurements show that DTCN molecules form self-assembled monolayers (SAMs) on gold via a thiolate link with the metallic substrate. Secondly, the DTCN SAM on gold is less ordered than the DT one as highlighted by SFG spectroscopy. Indeed, the intensities of the methyl vibration modes vanish while the methylene ones increase when DTCN molecules are adsorbed on the substrate instead of DT. We explain the differences in SAMs quality on the basis of STM measurements which reveal differences in molecular order and packing