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Table 1. Association equilibrium constants (K a ) with bovine α-chymotrypsin and bovine-trypsin of SFTI-1 analogues modified in the P1 or/and P1’ positionAnaloguetrypsinK a [M -1 ]chymotrypsinSFTI-1 wild (1.1 0.2) 10 10 (5.2±1.6)×10 6SFTI-1 (9.9 1.1) 10 9 (4.9±1.4)×10 6[Phe 5 ]SFTI-1 (2.0±0.2)×10 9[Nphe 5 ]SFTI-1 (3.9±0.3)×10 8[Phe 5 ,Ala 6 ]SFTI-1(1) (1.4±0.1)×10 8[Phe 5 ,Hse 6 ]SFTI-1 (2) (2.1±0.2)×10 8[Phe 5 ,Nhse 6 ]SFTI-1 (3) (3.4±0.6)×10 9[Nphe 5 ,Hse 6 ]SFTI-1 (4) (4.0±0.4)×10 7[Nphe 5 ,Nhse 6 ]SFTI-1 (5) (1.1±0.1)×10 8[Pro 6 ]SFTI-1 (6) (9.3±0.5)×10 7[Phe 5 ,Pro 6 ]SFTI-1 (7) (5.4±0.6)×10 7[Hyp 6 ]SFTI-1 (8) (6.4±0.2)×10 7[Phe 5 ,Hyp 6 ]SFTI-1 (9) (9.5±0.3)×10 7[Hpr 6 ]SFTI-1 (10) (9.8±0.8)×10 4[Phe 5 ,Hpr 6 ]SFTI-1 (11) (7.9±0.3)×10 4[Aze 6 ]SFTI-1 (12) (8.4±0.3)×10 7[Phe 5 ,Aze 6 ]SFTI-1 (13) (1.5±0.1)×10 8AcknowledgmentsThis work was supported by Ministry of Science and Higher Education (Grant No.2889/H03/2008/34).References1. Luckett, S., et al. J. Biol. Chem. 290, 525-533 (1999).2. McBride, J.D., et al. Biopolymers 66, 79-92 (2002).3 Łęgowska, A., et al. Bioorg. Med. Chem. 17, 3302-3307 (2009).471
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010The Influence of Disulfide Bridge of Trypsin Inhibitor SFTI-1for Enzyme – Inhibitor InteractionAnna Łęgowska, Dawid Dębowski, Magdalena Wysocka,Adam Lesner, and Krzysztof RolkaFaculty of Chemistry, University of Gdansk, Sobieskiego 18, Gdansk, 80-952, PolandIntroductionThe trypsin inhibitor SFTI-1 isolated in 1999 from the sunflower seeds by Luckett, et al.[1] is currently the smallest naturally occurring peptidic proteinase inhibitor. This peptidedisplays the strongest trypsin inhibitory activity among the Bowman-Birk family ofinhibitors. Owing to its small size (14 amino acid residues) and the well-defined structure(stabilized by head-to-tail cyclization and disulfide bridge), SFTI-1 has been chosen byseveral research teams to be a lead structure in the design of new inhibitors of serineproteinases. In order to investigate in detail the role of disulfide bridge in inhibitoryactivity, two series of SFTI-1 analogues were synthesized. In the first series of monocyclicSFTI-1 analogues, the disulfide bridge was formed by combination of Cys, Hcy, Pen andNhcy (N-sulfanylethylglycine) introduced at positions 3 and/or 11, originally occupied bythe Cys residues. In addition, in the substrate specificity P 1 position, peptoid monomersNlys and Nphe, resembling proteinogenic Lys and Phe, respectively were introducedinstead of Lys5. We have already proved [2] that both peptoid monomers areaccommodated well in the substrate pockets of trypsin and chymotrypsin, respectively. Inthe second series of monocyclic SFTI-1 analogues, a ring formation was achieved via aureido group incorporating the side-chain amino groups of L-2,3-diaminopropionic acid(Dap), L-2,4-diaminobutyric acid (Dab), Orn and Lys placed in positions originallyoccupied by Cys residues (Figure 1). The objective of the introduction of the set of dibasicamino acid residues starting with Dap (one CH 2 group) up to Lys (four CH 2 groups) in thepositions 3 and 11 was the determination of the optimal size of the SFTI-1 cycle/ring forthe inhibitor – trypsin interaction. In addition, unlike disulfide bridge, N-(ureidoethyl)-amide moieties are redox stable. This is a very important factor in case of introducing suchpeptides into the biological system.Fig. 1 Chemical structure of SFTI-1 analogues with carbonyl bridge, (x, y = 1 for Dap, 2for Dab, 3 for Orn and 4 for Lys).Results and DiscussionAll SFTI-1 analogues were synthesized by the solid phase method. Peptoid monomers(Nphe, Nlys(Boc) and Nhcy(Trt)) were introduced into the peptide chain by thesubmonomeric approach [3]. The carbonyl bridge was introduced in two step procedure.Dde and ivDde protecting groups were removed from side-chain amino functions of Orn,Lys, Dab and Dap, followed by reaction of bis(4-nitrophenyl) carbonate with free sidechainamino groups of peptidyl-resin [4]. Association equilibrium constants (K a ) ofsynthesized analogues with bovine -trypsin and bovine -chymotrypsin as well as theirproteolytic stability were determined. Details on synthetic methods and kineticinvestigations were described in our previous work [5].The results presented in Table 1 clearly indicated that Pen and Nhcy were notacceptable at the position 3, yielding inactive analogues, whereas another residue (Cys11)could be substituted without any significant impact on the affinity towards both ofexperimental enzymes. On the other hand, elongation of the Cys3 side chain by472
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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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