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1.
Claude Didierjean Julien Marin Emmanuel Wenger Jean‐Paul Briand Andr Aubry Gilles Guichard 《Acta Crystallographica. Section C, Structural Chemistry》2004,60(3):o200-o203
X‐ray studies reveal that tert‐butyl (6S)‐6‐isobutyl‐2,4‐dioxopiperidine‐1‐carboxylate occurs in the 4‐enol form, viz. tert‐butyl (6S)‐4‐hydroxy‐6‐isobutyl‐2‐oxo‐1,2,5,6‐tetrahydropyridine‐1‐carboxylate, C14H23NO4, when crystals are grown from a mixture of dichloromethane and pentane, and has an axial orientation of the isobutyl side chain at the 6‐position of the piperidine ring. Reduction of the keto functionality leads predominantly to the corresponding β‐hydroxylated δ‐lactam, tert‐butyl (4R,6S)‐4‐hydroxy‐6‐isobutyl‐2‐oxopiperidine‐1‐carboxylate, C14H25NO4, with a cis configuration of the 4‐hydroxy and 6‐isobutyl groups. The two compounds show similar molecular packing driven by strong O—H⋯O=C hydrogen bonds, leading to infinite chains in the crystal structure. 相似文献
2.
R. Arnaldi R. Averbeck K. Banicz J. Castor B. Chaurand C. Cicalo A. Colla P. Cortese S. Damjanovic A. David A. De Falco A. Devaux A. Drees L. Ducroux H. En’yo A. Ferretti M. Floris A. Foerster P. Force N. Guettet A. Guichard H. Gulkanian J. Heuser M. Keil L. Kluberg J. Lozano C. Lourenço F. Manso A. Masoni P. Martins A. Neves H. Ohnishi C. Oppedisano P. Parracho P. Pillot G. Puddu E. Radermacher P. Ramalhete P. Rosinsky E. Scomparin J. Seixas S. Serci R. Shahoyan P. Sonderegger H.J. Specht R. Tieulent G. Usai R. Veenhof H.K. Wöhri 《The European Physical Journal C - Particles and Fields》2007,49(1):235-241
The NA60 experiment at the CERN SPS has studied low-mass muon pairs in 158 A GeV In–In collisions. A strong excess of pairs
is observed above the yield expected from neutral meson decays. The unprecedented sample size close to 400000 events and the
good mass resolution of about 2% made it possible to isolate the excess by subtraction of the decay sources. The shape of
the resulting mass spectrum shows some non-trivial centrality dependence, but is largely consistent with a dominant contribution
from π+π-→ϱ→μ+μ- annihilation. The associated ϱ spectral function exhibits considerable broadening, but essentially no shift in mass. The
pT-differential mass spectra show the excess to be much stronger at low pT than at high pT. The results are compared to theoretical model predictions; they tend to rule out models linking hadron masses directly to
the chiral condensate.
PACS 25.75.-q; 12.38.Mh; 13.85.Qk 相似文献
3.
Poschalko A Lancelot N Marin J Larras V Limal D Elbayed K Raya J Piotto M Briand JP Guichard G Bianco A 《Chemistry (Weinheim an der Bergstrasse, Germany)》2004,10(18):4532-4537
A novel resin called DEUSS (perdeuterated poly(oxyethylene)-based solid support) has been prepared by anionic polymerization of deuterated [D4]ethylene oxide, followed by cross-linking with deuterated epichlorohydrin. DEUSS can be suspended in a wide range of solvents including organic and aqueous solutions, in which it displays a high swelling capacity. As measured by proton HRMAS of the swollen polymer, the signal intensity of the oxyethylene protons is reduced by a factor of 110 relative to the corresponding nondeuterated poly(oxyethylene)poly(oxypropylene) (POEPOP) resin, thus facilitating detailed HRMAS NMR studies of covalently linked molecules. This 1H NMR invisible matrix was used for the solid-phase synthesis of peptides, oligoureas, and a series of amides as well as their characterization by HRMAS NMR spectroscopy. On-bead NMR spectra of high quality and with resolution comparable to that of liquid samples were obtained and readily interpreted. The complete absence of the parasite resin signals will be of great advantage, for example, for the optimization of multistep solid-phase stereoselective reactions, and for the conformational study of resin-bound molecules in a large variety of solvents. 相似文献
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6.
Dr. Brice Kauffmann Dr. Gilles Guichard 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(44):15684-15692
Anion binding properties of neutral helical foldamers consisting of urea type units in their backbone have been investigated. 1H NMR titration studies in various organic solvents including DMSO suggest that the interaction between aliphatic oligoureas and anions (CH3COO?, H2PO4?, Cl?) is site‐specific, as it largely involves the urea NHs located at the terminal end of the helix (positive pole of the helix), which do not participate to the helical intramolecular hydrogen‐bonding network. This mode of binding parallels that found in proteins in which anion‐binding sites are frequently found at the N‐terminus of an α‐helix. 1H NMR studies suggest that the helix of oligoureas remains largely folded upon anion binding, even in the presence of a large excess of the anion. This study points to potentially useful applications of oligourea helices for the selective recognition of small guest molecules. 相似文献
7.
Katell Bathany Neil W. Owens Gilles Guichard Jean-Marie Schmitter 《Journal of the American Society for Mass Spectrometry》2013,24(3):458-462
This study is focused on sequence analysis of peptidomimetic helical oligoureas by means of tandem mass spectrometry, to build a basis for de novo sequencing for future high-throughput combinatorial library screening of oligourea foldamers. After the evaluation of MS/MS spectra obtained for model compounds with either MALDI or ESI sources, we found that the MALDI-TOF-TOF instrument gave more satisfactory results. MS/MS spectra of oligoureas generated by decay of singly charged precursor ions show major ion series corresponding to fragmentation across both CO-NH and N′H-CO urea bonds. Oligourea backbones fragment to produce a pattern of a, x, b, and y type fragment ions. De novo decoding of spectral information is facilitated by the occurrence of low mass reporter ions, representative of constitutive monomers, in an analogous manner to the use of immonium ions for peptide sequencing. 相似文献
8.
Isabelle Déléris Anne Saint‐Eve Etienne Sémon Hervé Guillemin Elisabeth Guichard Isabelle Souchon Jean‐Luc Le Quéré 《Journal of mass spectrometry : JMS》2013,48(5):594-607
For the on‐line monitoring of flavour compound release, atmospheric pressure chemical ionization (APCI) and proton transfer reaction (PTR) combined to mass spectrometry (MS) are the most often used ionization technologies. APCI‐MS was questioned for the quantification of volatiles in complex mixtures, but direct comparisons of APCI and PTR techniques applied on the same samples remain scarce. The aim of this work was to compare the potentialities of both techniques for the study of in vitro and in vivo flavour release. Aroma release from flavoured aqueous solutions (in vitro measurements in Teflon bags and glass vials) or flavoured candies (in vivo measurements on six panellists) was studied using APCI‐ and PTR‐MS. Very similar results were obtained with both techniques. Their sensitivities, expressed as limit of detection of 2,5‐dimethylpyrazine, were found equivalent at 12 ng/l air. Analyses of Teflon bag headspace revealed a poor repeatability and important ionization competitions with both APCI‐ and PTR‐MS, particularly between an ester and a secondary alcohol. These phenomena were attributed to dependency on moisture content, gas/liquid volume ratio, proton affinities and product ion distribution, together with inherent drawbacks of Teflon bags (adsorption, condensation of water and polar molecules). Concerning the analyses of vial headspace and in vivo analyses, similar results were obtained with both techniques, revealing no competition phenomena. This study highlighted the equivalent performances of APCI‐MS and PTR‐MS for in vitro and in vivo flavour release investigations and provided useful data on the problematic use of sample bags for headspace analyses. Copyright © 2013 John Wiley & Sons, Ltd. 相似文献
9.
Lorne Tallet Emilie Frisch Mgane Bornerie Claire Medemblik Benoît Frisch Philippe Lavalle Gilles Guichard Cline Douat Antoine Kichler 《Molecules (Basel, Switzerland)》2022,27(5)
There is an urgent need to develop new therapeutic strategies to fight the emergence of multidrug resistant bacteria. Many antimicrobial peptides (AMPs) have been identified and characterized, but clinical translation has been limited partly due to their structural instability and degradability in physiological environments. The use of unnatural backbones leading to foldamers can generate peptidomimetics with improved properties and conformational stability. We recently reported the successful design of urea-based eukaryotic cell-penetrating foldamers (CPFs). Since cell-penetrating peptides and AMPs generally share many common features, we prepared new sequences derived from CPFs by varying the distribution of histidine- and arginine-type residues at the surface of the oligourea helix, and evaluated their activity on both Gram-positive and Gram-negative bacteria as well as on fungi. In addition, we prepared and tested new amphiphilic block cofoldamers consisting of an oligourea and a peptide segment whereby polar and charged residues are located in the peptide segment and more hydrophobic residues in the oligourea segment. Several foldamer sequences were found to display potent antibacterial activities even in the presence of 50% serum. Importantly, we show that these urea-based foldamers also possess promising antifungal properties. 相似文献
10.
Yella-Reddy Nelli Céline Douat-Casassus Paul Claudon Brice Kauffmann Claude Didierjean Gilles Guichard 《Tetrahedron》2012,68(23):4492-4500
A new N-Boc-protected monomer for the synthesis of oligourea foldamers containing the (1H-imidazolyl-4yl)methyl side chain of histidine, has been prepared in seven steps from Trt-His(τ-Trt)-OMe. This protecting group combination on histidine was found to be critical to ensure efficient access to the requisite activated building block. This new derivative, suitable for solid phase synthesis, expands the current arsenal of building blocks with proteinogenic side chains useful for the design of peptidomimetic oligourea foldamers. 相似文献