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According to HPLC, purity of the crude products isolated by extraction and standardwashing procedure were found in the range 91-96%.Bu(Ph)O(Ph)Bu+ PBu(Ph)O RR-SO -1 O3 RN N1 -COOHNH 2 -R 2N NR1O N OO N O5a-i 6 7Fig. 3. Synthesis of peptides by using 5.NHR 2Table 1. Peptide synthesis using 5b and 5f as coupling reagentsActivationCoupling reagents Dipeptidetime [min]Yield [%]DMT/Bu 3 P/TsO -(5b)DMT/PPh 3 /TsO -(5f)Z-Ala-Phe-OMe88Z-Ala-Gly-OMe 86Z-Ala-Aib-OMe 87Z-Ala-Tyr-OMe 8230Z-Ala-Ser-OMe 85Fmoc-Ala-Leu-OMe 89Fmoc-Ala-Phe-OMe 88Fmoc-Phe-Ala-OMe 82Z-Aib-Aib-OMe81Z-Ala-Gly-OMe 84Z-Ala-Aib-OMe 83Z-Ala-Tyr-OMe 78Z-Ala-Phe-OMe 80Z-Phe-Aib-OMe4581Z-Ala-Ser-OMe 82Fmoc-Ala-Leu-OMe 83Fmoc-Ala-Phe-OMe 80Fmoc-Phe-Ala-OMe 79AcknowledgmentsThis work was supported by Ministry of Science and Higher Education, under the Research Project: NN204 228734.References1. a) Kamiński, Z.J., Kolesińska, B., Kolesińska, J., Sabatino, G., Chelli, M., Rovero, P., Błaszczyk,M., Główka, M.L., Papini, A.M. J. Am. Chem. Soc. 127, 16912-16920 (2005); b) Kolesińska, B.,Frączyk, J., Papini, A.M., Kamiński, Z.J. Chemistry Today 25, 26-29 (2007).125
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Triazine Condensing Agents for Synthesis of Peptide Bond inAqueous MediaKrzysztof J. Zajac, Ireneusz Kaminski, Justyna Fraczyk, andZbigniew J. KaminskiInstitute of Organic Chemistry, Technical University of Lodz, 90-924, Lodz, PolandIntroductionSuccessful synthesis of the peptides bond in aqueous media still remains a challengealthough several attempts have been made to resolve the problems [1]. To perform peptidesynthesis in water, the coupling reagent must be water-soluble, maintain solubility andreactivity of intermediate products, preserve enantiomeric homogeneity of products instrongly polar environment and form conveniently removable waste (if any) in order tofacilitate isolation of the main product. The pursuit for aqueous-compatible couplingreagent is promoted both by environmental problem of the safe disposal of large amountsof organic solvents required for SPPS, as well as by demand for efficient method useful formodification of complex molecules, incompatible with organic solvents, such as proteinsand carbohydrates.Results and DiscussionCoupling reagents were prepared in two subsequent stages by treatment 2,4-dichloro-6-methoxy-1,3,5-triazine (1) with aromatic and aliphatic aminosulphonic acids [2] in thepresence of base, followed by quaternization of reactive intermediate in reaction withNMM and formation of zwitterionic final products 2a-f. Activation of N-protectedcarboxylic components with 2a-f proceeded in aqueous solution or in water miscibleorganic solvent affording water soluble intermediates 3a-f due to the presence of sulphonicgroup (Figure 1).ORCl1) H 2 N X SO 3 H / NaHCO 3N +HNOHN N2) O NN NPG OMeO N Cl1THF/waterMeO NXN SO3-H2a-fX = alkyl, arylOHNPG ORN NMeO NX -N SOH33a-fsubstrates with standard protecting groups(PG) become soluble in aqueous mediaFig. 1. Synthesis of water-soluble coupling reagents 2a-f and activation of N-protectedcarboxylic component.It has been observed that the structure of aminosulphonic acids have an effect on theefficiency of 2a-f (see Figure 2). The most versatile as coupling reagent has been found 2a,which was obtained from 4-aminobenzenesulphonic acid. Its structure was confirmed byX-ray analysis.MeOMeONNNNN + MeO2aNN HNN + MeO2dN Hyield: 88%yield: 88%OSO OOOSOMeOMeONNNNN + MeO2bNN HNN + MeO2eN Hyield: 62%yield: 69%OOSOOSOOMeOMeONNNNN + MeO2cNNMeN +ON HO S Oyield: 72%N HOOSOyield: 68%O2fFig. 2. Coupling reagents 2a-f for peptide synthesis in aqueous media.126
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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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A) PSA, few seconds73B) PSA, 45 min
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short β strands. In contrast, nume
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neg. control Cs9-Rhd MM-218Fig. 2.
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Table 1. The general structure of t
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% ID in the liver 1 h p.i.100908070
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Peptidyl phosphoranes were first re
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obtained from the same sardines and
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MccJ25 variants were produced by si
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Fig. 2. Proposed signaling mechanis
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Table 1. mCD4-HS12 antiviral activi
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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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