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Table 1. Coupling conditions for the synthesis of peptide 1EntryCouplingTime, Temp. a Coupling reagent Equiv.Purity(HPLC)1 60 min, RT DIC/HOAt 3
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010The Oxime-Based Family of Coupling ReagentsRamon Subirós-Funosas 1,2 , Ayman El-Faham 1,3 , andFernando Albericio 1,2,41 Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10,Barcelona, 08028, Spain; 2 CIBER-BBN, Networking Centre on Bioengineering,Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, Barcelona,08028, Spain; 3 Department of Chemistry, Faculty of Science, Alexandria University,Ibrahimia, 21321, Egypt; 4 Department of Organic Chemistry, University of Barcelona,Martí i Franquès 1-11, Barcelona, 08028, SpainIntroductionHOBt and other parent benzotriazoles show explosive properties, a feature that isincreasingly limiting their commercial availability. Consequently, alternative scaffolds arerequired for safe and efficient amide bond formation. A few decades ago, several stable andacidic ketoximes were proposed as additives, although with little success because of thelack of relevant data [1,2]. Recently, exhaustive studies on ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma, 1), and the derived uronium salt, bearing a dimethylmorpholinocarbocation skeleton (COMU, 2), have proved that oximes are indeed a reliable choice ascoupling reagents (Figure 1) [3,4]. Thus, here we further studied the potential of oximebasedcompounds by testing new reactive phosphonium and uronium salts, along withnovel Fmoc- and Alloc-oxime carbonates.Results and DiscussionTwo tris(pyrrolidino)phosphonium salts of Oxyma were easily obtained in 75-80% yield ina one-pot fashion by reaction of its potassium salt with a bromotris(pyrrolidino)phosphonium salt, obtaining either the hexafluorophosphate (PyOxP, 3) ortetrafluoroborate (PyOxB, 4) versions (Figure 2, left)[5]. The higher stability of PyOxP (commerciallyknown as PyOxyme) than PyOxB confers the reagentgreater suitability in the assembly of peptide fragmentsor cyclizations. PyOxyme also combined impressivesolubility with high stability, compared with knownbenzotriazole-based PyAOP, PyBOP and PyClock. Inaddition, PyOxyme induced outstanding control ofoptical purity and shows high efficiency in theFig. 1. Structure of Oxyma andCOMU.assembly of sterically demanding linear sequences.Last but not least, PyOxyme afforded the highestpercentage of target peptide during cyclization studies,exceeding the performance of PyAOP (Table 1).Fig. 2. Structure of oxime-based coupling and alkyloxycarbonyl-introducing reagents.176
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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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Proceedings of the 31 st European P
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RT: 0,00 - 5,9936000034000032000030
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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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