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Lena G Lallemand E Gruner AC Boeglin J Roussel S Schaffner AP Aubry A Franetich JF Mazier D Landau I Briand JP Didierjean C Rénia L Guichard G 《Chemistry (Weinheim an der Bergstrasse, Germany)》2006,12(33):8498-8512
The development of the 1,3,5-triazepane-2,6-dione system as a novel, conformationally restricted, and readily accessible class of dipeptidomimetics is reported. The synthesis of the densely functionalized 1,3,5-triazepane-2,6-dione skeleton was achieved in only four steps from a variety of simple linear dipeptide precursors. To extend the practical value of 1,3,5-triazepane-2,6-diones, a general polymer-assisted solution-phase synthesis approach amenable to library production in a multiparallel format was developed. The conformational preferences of the 1,3,5-triazepane-2,6-dione skeleton were investigated in detail by NMR spectroscopy and X-ray diffraction. The ring exhibits a characteristic folded conformation which was compared to that of related dipeptide-derived scaffolds including the more planar 2,5-diketopiperazine (DKP). Molecular and structural diversity was increased further through post-cyclization appending operations at urea nitrogens. Preliminary biological screens of a small collection of 1,3,5-triazepane-2,6-diones revealed inhibitors of the underexplored malaria liver stage and suggest strong potential for this dipeptide-derived scaffold to interfere with and to modulate biological pathways. 相似文献
44.
We have measured the current-voltage characteristics of a single Josephson junction placed in a high impedance environment. The transfer of Cooper pairs through the junction is governed by overdamped quasicharge dynamics, leading to Coulomb blockade and Bloch oscillations. Exact duality exists to the standard overdamped phase dynamics of a Josephson junction, resulting in a dual shape of the current-voltage characteristic, with current and voltage changing roles. We demonstrate this duality with experiments which allow for a quantitative comparison with a theory that includes the effect of fluctuations due to the finite temperature of the electromagnetic environment. 相似文献
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Bianco A Fournel S Wieckowski S Hoebeke J Guichard G 《Organic & biomolecular chemistry》2006,4(8):1461-1463
The C3-symmetric molecule has been previously shown to mimic CD40 ligand (CD40L) homotrimers and to display effector functions. This molecule consists of a cyclic hexapeptide core containing the repetition of the D-Ala-L-Lys motif. The side chains of the lysine residues have been modified by appending the CD40L-derived sequence 143Lys-Gly-Tyr-Tyr146 via a 6-aminohexanoic acid residue as a spacer. The present report describes a general solid-phase synthesis approach to and related trimeric architectures. In addition, their CD40 binding properties as well as their effector functions have been evaluated. 相似文献
46.
Marin J Didierjean C Aubry A Briand JP Guichard G 《The Journal of organic chemistry》2002,67(24):8440-8449
The synthesis of (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylates (5) and related (3S,6R)-3-hydroxy-6-alkyl-2-oxo-1-piperidinecarboxylates has been developed. The approach is based on the asymmetric hydroxylation of enolates generated from the corresponding N-protected-6-substituted piperidin-2-ones. The utility of 5a as a precursor in the synthesis of (2S,5R)-5-hydroxylysine (1), an amino acid unique to collagen and collagen-like proteins, has also been demonstrated. (2S)-6-oxo-1,2-piperidinedicarboxylates (6) required for hydroxylation studies were prepared in 38-74% yield, starting from conveniently protected aspartic acid as inexpensive chiral adduct. Hydroxylation of 6 to 5 proceeds in high yield and excellent diastereoselectivity by treatment of their Li-enolate with (+)-camphorsulfonyloxaziridine at -78 degrees C. Ring opening of di-tert-butyl (2S,5R)-6-oxo-1,2-piperidinedicarboxylate ((5R)-5a) under reductive conditions afforded the corresponding 1,2-diol (17) in 91%, which was further transformed to (2S,5R)-5-hydroxylysine in four steps (84%). 17 is also a versatile intermediate in the preparation of tert-butyl (2S,5R)-2-[(tert-butoxycarbonyl)amino]-5-hydroxy-6-iodohexanoate (3) and tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[(2R)-oxiranyl]butanoate (4), two amino acid derivatives used in the total synthesis of the bone collagen cross-link (+)-pyridinoline (2a). 相似文献
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R. H. Chittenden E. Bauer C. J. Lintner H. Ost P. Guichard L. Sostegni G. Düll Alb Munsche A. L. Winton Jr. O. Reinke H. Schreib J. Berger J. Krieger A. von Asboth C. Monheim F. Seyfert A. Leclerc Effront A. Baudry O. Saare W. E. Stone F. Mylius H. B. Stocks C. Meineke A. Girard F. W. Küster M. Dennstedt F. Voigtländer G. Ambühl W. Keller F. W. Dafert A. Meyer Em. Bourguelot und Stoltz 《Fresenius' Journal of Analytical Chemistry》1896,35(1):607-623
Ohne Zusammenfassung 相似文献
49.
Guichard C. F. Cross E. J. Bevan Leo Liebermann und Himly 《Fresenius' Journal of Analytical Chemistry》1883,22(1):70-71
Ohne Zusammenfassung 相似文献
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