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ONH 2CHCNSONHH 2COCH 2COCH 2CH 2NCH 2OSSNCCHHNCOH 2COFigure 2A: Structure of morpholinoaspartic acid and morpholinolysineOOOONHCHCNSCHNCHCNSH 2CCH 2CH 2COCH 2NOCH 2SHNOFigure 2B: Structure of morpholinoaspartic acid and morpholinolysine monomersFig. 2. Structure of morpholinoaspartic acid and morpholinolysine (A) and acrylic acidmodified monomers (B).Results and DiscussionHerein, we report the creation of new hybrid materials with bactericide and bacteriostaticproperties based on modified amino acid, incorporated in polymer matrices. Two aminoacids (Asp and Lys) were chosen to be modified by thiomorpholine incorporation. Thischoice was done because of both their different properties (the first one is acid and thesecond one is basic) and literature data that they could be used as a media for bacteriaproliferation. Compounds presented in Figure 2A and 2B were synthesized. Thesecompounds were synthesized using standard coupling procedures in solution by means ofTBTU as a coupling reagent. In order to obtain acrylamide derivatives of modified aminoacids which can be further polymerized and a new hybrid material to be created, thechloride of acrylic acid was incorporated to N -amino group of Asp and Lys modified withthiomorpholine. A Schotten-Baumann reaction was used in presence of Et 3 N as a base. Thepolymerizations were induced by AIBN (azobisisobutyronitrile) in DMF at 60 o C.The studies of visco-elastic properties of newly synthesized matrices are in progress.A new technique employing shear waves in the ultrasound range (the so-called “ThicknessShear Mode” technique) is used [7]. This technique is a sensitive method to detect themodification of the structure of the polymer during its formation. It allows to track therheological parameters of a polymer matrices during the process of formation under theliquid to gel phase by investigation of the following parameters:- the complex shear modulus (G’( ), G”( ) at high frequency giving informationabout the viscoelasticity of the polymer.- the complex permittivity ( ’( ), ”( )) in the radiofrequency region.References1. Setareh, M., Javaherdashti, R. Mater. Corrosion 54, 259-263 (2003).2. Little, B.J., Wagner, P. Mater. Perf. 36, 40-44 (1997).3. Cooling Water Treatment Manual, 3rd ed., TPC1 Publication, NACE International Publications,Houston, TX.4. The Institute of Materials, U.K. A Working Party Report on Microbiological Degradation ofMaterials and Methods of Protection, European Federation of Corrosion Publication No. 9, 1992.5. Flemming, H.-C. Economical and Technical Overview, Microbially Influenced Corrosion ofMaterials, E. Heitz, H.-C. Flemming, W. Sand, Ed., Springer-Verlag, Berlin, 1996.6. Poupin, P., et al. Applied and Environmental Microbiology 64, 159-165 (1998).7. Ould-Ehssein, C., et al. Ultrasonics 44, 875-879 (2006).71
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Convenient Synthesis of Tfm-Dipeptides from UnprotectedEnantiopure α-Tfm-Proline and α-Tfm-AlanineGrégory Chaume, Nathalie Lensen, Caroline Caupène, andThierry BrigaudLaboratoire SOSCO, Université de Cergy-Pontoise, 5, mail Gay Lussac,Cergy-Pontoise, F-95000, FranceIntroductionThe major disadvantages of peptides as therapeutic agents are their rapid degradation bypeptidase and their low lipophilicity. In this context, α-trifluoromethyl-α-amino acids(α-Tfm-AAs) are very attractive compounds for the design of biologically active molecules[1]. Their incorporation into peptides increases chemical and thermal stability, resistance toprotease degradation and enhances hydrophobicity giving a better affinity for lipidmembranes [2]. Moreover, their incorporation into peptides induces particularconformational stabilisations and better auto-assembly [3]. In addition, labeled 19 F peptidesare of a big interest for structure elucidation and biochemical process investigations [4]. Inthe course of our studies, we have recently reported efficient and scalable methodologiesfor the synthesis of enantiopure α-Tfm-AAs [5-9]. Here, we report the synthesis of highlylipophilic dipeptide building blocks from enantiopure α-Tfm-AAs [10].Results and DiscussionThanks to a convenient gram-scale strategy for the synthesis of (S)- and (R)-α-Tfm-prolines[12], we were able to undertake a methodological study in order to incorporate thispromising unnatural amino acid in a peptide chain. We anticipated that α-Tfm-AAs shouldbe deployable in peptide coupling reactions without protection of their nitrogen atoms dueto the strong deactivation of the amino group by the CF 3 group. The peptide couplingmethodological study allowed us to establish the best coupling conditions to avoid theformation of the diketopiperazine side product and to optimize the coupling yield. Thus,one equivalent of α-Tfm-proline is added to two equivalent amount of the non-fluorinatedamino acid in the presence of the coupling reagents HOBt/EDCI. These optimizedconditions were then successfully applied to the coupling of various amino acids withunprotected α-Tfm-proline (Figure 1). The enantiopure dipeptides derived fromunprotected (S)-α-Tfm-proline and alanine, valine, phenylalanine and leucine wereconveniently obtained in good yields (76-95%) without any traces of diketopiperazine. Thecoupling reaction starting from unprotected (R)-α-Tfm-proline was also very efficient.In order to extend the methodology to acyclic α-Tfm-AAs, the coupling of α-Tfmalanine[8] was investigated. Coupling reactions between unprotected (R)-α-Tfm-alanineand non-fluorinated α-amino acids were achieved following the same procedure designedfor α-Tfm-proline. The corresponding dipeptides were conveniently obtained in 77-82%isolated yields without formation of diketopiperazine (Figure 2).As a proof-of-concept of the incorporation of enantiopure α-Tfm-AAs into peptidechains, coupling reaction of the (R)-α-Tfm-Ala-L-Leu-OBn dipeptide at its N-terminus wasFig. 1. α-Tfm-Proline containing dipeptides.72
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Peptides 2010Tales of PeptidesProce
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Peptides 2010Tales of PeptidesProce
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IntroductionWe had the distinct hon
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Scientific programIn planning the 3
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31 st EUROPEAN PEPTIDE SYMPOSIUMSep
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published by John Wiley & Sons as a
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The Josef Rudinger AwardThis award
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Young Investigators' SymposiumThe y
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xxiv
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Design of Peptidyl-Inhibitors for G
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Synthetic Antifreeze Glycopeptide A
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Synthesis and Oxidative Folding of
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Convergent Syntheses of Huprp106-12
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Bactericidal Activity of Small Beta
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Bradykinin Analogues Acylated on Th
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Antimicrobial Activity of Small 3-(
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Interaction of Curcumin with A-Synu
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Fluorescent and Luminescent Fusion
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Cellular Expression of the Human An
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2D IR Spectroscopy of Oligopeptides
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large, non-redundant subset of prot
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The aberrantly glucosylated peptide
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Table 1. Proline cis/trans ratios o
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Table 1. Yields, UV-vis absorption
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Table 1. Purity of the targeted tri
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processes are blocked. Interestingl
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(tb4 n ,1 m )MTII(tb1 n ,4 m )MTIIF
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Fig. 2. a) Part of the 400 MHz HR-M
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Once printed, the amino acid partic
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Subject index(S)-2-(1-adamantyl)gly
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chip 18chiral triazine condensing r
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heat stress 348helical conformation
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O-acyl isopeptide method 112obesity
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SH2-ligands 210short collagen-relat
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Author indexAboye, Teshome Leta 142
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Chi, Hongfang 480Chiche, Laurent 6C
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Geronikaki, Athina 444Gessmann, Ren
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Kostova, Kalina 528Kotzia, Georgia
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Nagata, Koji 162Nagayev, Igor Yu. 5
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Salvarese, Nicola 518Sammet, Benedi
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Vauquelin, Georges 138Veiga, Ana Sa
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