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HNOHOHOHOHNOHOAcNHO OHOOOHNH 2HO HO H HOH ONHH NH NHHNH NHHH NH NHNHOOOOCH 3 HOHOOH1 (from solid-phase peptide synthesis)NH 2CH 3H O HNHH NH NOONH 2HONHOHHNHOHHOHOOUDP-Gal1,3-GalTOHNHOHNO OHOHHO HNHH NH NHHOOOOH2O HHNHHOHNHOOHOH OH OHOOOOHAcNHOO NH 2O H OH NH NHNHOCH 3 HOHNH 2CH 3H O HNHH NH NOONH 2HONHOHHNHOHHOHOOCMP-Neu5Ac2,3-STHOAcHNHOHO HOOOCOOHOHOHOOHOH OHOOAcNHOHHNOHOHNOHHOO OHO HNHH NH NHHOOOH3O HHNHOO NH 2HO H ONHH NH NHNHOOCH 3 HOHNH 2CH 3H O HNHH NH NOONH 2HONHHNHOHHOHOOScheme 1. Enzymatic synthesis of glycopeptide 3.Fig. 1. MALDI-MS of glycopeptide 3.References1. Craig, A.G., Norberg, T., Griffin, D., Hoeger, C., Akhtar, M., Schmidt, K., Low, W., Dykert, J.,Richelson, E., Hillyard, D., Imperial, L., Cruz, L.J., Olivera, B.M. J. Biol. Chem. 274, 13752-13759(1999).2. Lüning, B, Norberg, T. Glycoconjugate J. 6, 5-19 (1989).421
<strong>Proceedings</strong> of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Active Peptidomimetic Insect Kinin Analogs with Type VI TurnMotif 4-Aminopyroglutamate Lack Native Peptide BondsKrzysztof J. Kaczmarek 1,2 , Geoffrey M. Coast 1,3 , Janusz Zabrocki 1,2 ,and Ronald J. Nachman 1*1 Areawide Pest Management Research Unit, Southern Plains Agricultural ResearchCenter, U.S. Department of Agriculture, College Station, TX, 77845, U.S.A.; 2 Institute ofOrganic Chemistry, Technical Universtiy of Lodz, 90-924, Poland; 3 School of Biologicaland Chemical Sciences, Birkbeck College, London, WC1E 7HX, U.KIntroductionInsect neuropeptides of the insect kinin class share a <strong>com</strong>mon C-terminal pentapeptidesequence Phe 1 -Xaa 2 -Xbb 3 -Trp 4 -Gly 5 -NH 2 (Xaa 2 = Asn, His, Phe, Ser or Tyr; Xbb 3 = Pro,Ser or Ala) and has been isolated from various insects [1,2]. It has been reported that thesepeptides regulate such critical physiological processes as water and ion balance, hindgutmotility, and digestive enzyme release [1]. The C-terminal sequence is all that is required toelicit a physiological response in hindgut myotropic and cricket Malpighian tubulesecretion assays [1]. The active core sequence Phe 1 -Tyr 2 -Pro 3 -Trp 4 -Gly 5 -NH 2 is equipotentwith the parent nonapeptide (SGADFYPWGa) in these two assays. Conformational studiessuggest that the active conformation adopted by the C-terminal pentapeptide active core ofthe insect kinins at the cricket Malpighian tubule receptor site is the cis-Pro type VI -turnover residues 1-4 [1-3]. Analogs incorporating the tetrazole and 4-aminopyroglutamate(APy) motifs, mimics of a cis-peptide bond and a type VI -turn (Figure 1), elicitedsignificant diuretic activity and provided evidence for this preference in activeconformation [1-3]. An evaluation of all four stereochemical variants of the APy motif inthe insect kinin core sequence in the cricket Malpighian tubule secretion assay revealed thatthe analog (2R,4S)-APy (EC 50 = 7 x 10 -9 M) was an order of magnitude more potent thanthe other three analogs, including the parent analog (2S,4S)-APy (EC 50 = 1.4 x 10 -7 M)[3].* ** ***NNNNNNOHOHTETRAZOLE4-AMINOPYROGLUTAMIC ACIDFig 1. Comparison of structures of the tetrazole and 4-aminopyroglutamate (APy) motifs,mimics of a cis-peptide bond.Unfortunately, insect kinin peptides are unsuitable as pest control agents and/or researchtools for insect neuroendocrinologists due to susceptibility to degradation by both exo- andendo-peptidases in the hemolymph (blood) and gut, as well as an inability to efficientlypenetrate the outside cuticular layer of the insect. Two susceptible hydrolysis sites in insectkinins [4] have been reported. The primary site is between the Pro 3 and Trp 4 residues andthe secondary site is N-terminal to the Phe 1 residue in natural, extended insect kininsequences. In this study, we synthesized simplified mimetic analogs of the insect kininC-terminal pentapeptide core that incorporate the (2R,4S)-APy (Apy) and (2S,4S)-APy(APy) motifs, a reduced peptide bond linkage ([r]) between residues Trp 4 -Gly 5 , and featurea hydrocinnamyl (Hca) group as a replacement and mimic of the Phe 1 residue. The twoanalogs (Hca-APy-Trp[r]Gly-NH 2 [1796] and Hca-Apy-Trp[r]Gly-NH 2 [1797]) wereevaluated on the cricket Malpighian tubule fluid secretion assay. The biostable, mimeticanalogs contain no native peptide bonds that would be susceptible to degradation byinternal peptidases.Results and DiscussionFollowing synthesis of the two stereochemical variant insect kinin mimetic analogs 1796and 1797 containing (2S,4S)-APy (APy) and (2R,4S)-APy (Apy), respectively, they wereevaluated on isolated Malpighian tubules of the house cricket Acheta domesticus to422
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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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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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