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1+H 2O1RHHCOH 1 2HC N C COOHRHCHOHC N C COOH2 2 HRR-H 2O+H 2O-H 2O121N RR N R1a2a2R 2R O OO OTautomerismTautomerism1 211b N RR N R2b2R O OHO OHH 11c N RH 1 2cCHO N R(ARP)(HRP)OO2OR O OFig. 1. Proposed racemization of amino acid (AA) enantiomers. Shown are general openchainstructures of Schiff bases resulting from the reaction of AAs with aldoses 1(seriestriose to hexanoses) or (hydroxyalkyl)aldehydes, or ketoses 2 (series tetrulose to hexuloses)or (hydroxyalkyl)ketones. Tautomerism of -lactones 1a, 1b and 2a, 2b formed from 1 and2, respectively, are displayed. Structures of the rearrangement products generated from 1and 2 are shown in 1c (ARP) and 2c (HRP). R 1 = AA side chain; R 2 = sugar residues; formethylglyoxal monohydrate (1,2-dihydroxyacetone) R 2 = methyl in 2, 2a and 2b and twohydroxyl groups are bound to C 1 of 2.AcknowledgmentSpecial thanks to Prof. Carlo Unverzagt, University of Bayreuth, for valuable discussion ofmechanistic aspects at the occasion of the 31 EPS.References1. Brückner, H., Justus, J., Kirschbaum, J. Amino Acids 21, 429-433 (2001).2. Brückner, H., Kirschbaum, J., Pätzold, R. In Benedetti, E., Pedone, C. (Eds.) Peptides 2002(Proceedings of the 27 th European Peptide Symposium), Edizioni Ziino, Napoli, 2002, p. 54-55.3. Hofmann, T. Eur. Food Res. Technol. 209, 113-121 (1999).4. Pätzold, R., Brückner, H. Eur. Food Res. Technol. 223, 347-354 (2006).5. Pätzold, R., Brückner, H. Amino Acids 31, 63-72 (2006).6. Kim, J.-S., Lee, Y.-S. Food Chemistry 108, 582-592 (2008).65
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Nicotianamine and Thermonicotianamine: Supported Synthesisand Chelation AbilityManuel Larrouy, Jean Martinez, and Florine CavelierInstitut des Biomolécules Max Mousseron, UMR 5247 CNRS-UM1-UM2, Place E.Bataillon, Case Courrier 1703, 34095, Montpellier, FranceIntroductionThe nicotianamine (NA), which was first isolated from the leaves of Nicotiana Tabacum L[1] is known as a key biosynthetic precursor of phytosiderophores. Various studies haveproved that NA plays a significant role in the plants physiology as iron, nickel or zinctransporter [2].Due to the importance of NA, we developed a new method to provide easily andquickly synthetic NA [3-9] and analogues for structure-activity relationship studies on thecomplementation of Nicotianamine Synthase (NAS) deficient tomato mutant“Chloronerva”. Using this method, we also synthesized a new natural analogue of NA, thethermonicotianamine (tNA) [10], that was found in the active site of an archeal NAS likeenzyme [11-12]. Chelating ability of this compound was compared to that of NA by MSanalysis of metal-ligand complexes [13].Results and DiscussionThis novel approach involved a first moiety anchored on Wang resin and bearing a freeamine and on the other part, an aldehyde with suitable protecting groups on all otherfunctions (Scheme 1). This later building block will be used twice to construct NA from theleft to the right part of the molecule (Scheme 2). This new method provided NA, the newnatural analogue tNA and non-natural analogues in high yields and purity.Scheme 1. Synthesis of the aldehyde moiety.Scheme 2. Supported synthesis of Nicotianamine.Chelating ability of tNA was investigated and compared to that of NA by MS analysis. Itappeared that NA and tNA are able to chelate quantitatively Cu(II), Ni(II) (Figures 1 and 2)and Co(II) at pH = 7.5. Competition studies of metal chelation with NA and tNA showedthat Cu(II) complexes are formed first, whereas Ni(II) complexes are thermodynamicallymore stable. Moreover tNA seemed to chelate Cu(II) preferentially.66
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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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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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