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large, non-redundant subset of proteinstructures determined to high resolution(Figure 3). Moreover, these studies indicatedthat n→π* interactions are abundant andespecially prevalent in common secondarystructures such as α-, 3 10 -, and polyproline IIhelices, and twisted β-sheets. As the adjacentcarbonyl dipoles repel each other in anα-helix, the n→π* interaction likely plays animportant role in helix nucleation. Othersignatures of the n→π* interaction such aspyramidalization of the acceptor carbonylcarbon [9], considerable carbonyl bondlengthening [10], and polarization of itsπ-electron cloud [10] have been observed inthe α-helices of high-resolution proteinstructures. Occasionally, β-strands have abulge - an amplified right-handed twist -Fig. 3. Ramachandran map of n→π*interactions (gray) in proteins [8].resulting in local disruption of the β-sheet structure. Such β-bulges are involved in thedimerization of immunoglobulin domains and can assist in enclosing the active sites ofproteins. Two common types of β-bulges, the G1 and wide types, adopt ϕ and ψ dihedralangles indicative of considerable n→π* interactions. The conformational stability of thecollagen triple helix has already been attributed in part to the n→π* interaction [11].Interestingly, the absence of 4S diastereomer of hydroxyproline from collagen has beenattributed in part to a strong n→π* interaction that provides it with unusual conformationalfeatures [12].In addition to its widespread occurrence in proteins, the n→π* interaction has beenpostulated to play an important role in the origin of life [13] as well as modulating theconformational and physical properties of aspirin [9]. Finally, we note that n→π*electronic delocalization likely plays a role in many protein–ligand interactions andcatalytic processes.AcknowledgmentsThis work was supported by grant R01 AR044276 (NIH). We thank Profs. G.R. Krow, S.J. Miller, J.D.Sutherland, and D.N. Woolfson for collaborative interactions, and F.W. Kotch, I.A. Guzei, L.C.Spencer, B.R. Caes, C.N. Bradford, and M.D. Shoulders for contributive discussions.References1. Anfinsen, C.B. Science 181, 223-230 (1973).2. (a) DeRider, M.L., et al. J. Am. Chem. Soc. 124, 2497-2505 (2002); (b) Hinderaker, M.P., Raines,R.T. Protein Sci. 12, 1188-1194 (2003); (c) Hodges, J.A., Raines, R.T. Org. Lett. 8, 4695-4697(2006); (d) Choudhary, A. et al. J. Am. Chem. Soc. 131, 7244-7246 (2009).3. Weinhold, F. Adv. Protein Chem. 72, 121-155 (2005).4. (a) Diederich, F. et al. Angew. Chem. Int. Ed. 44, 1788-1805 (2005); (b) Diederich, F., et al. Proc.Natl. Acad. Sci. U.S.A. 105, 17290-17294 (2008).5. (a) Milner-White, E.J., et al. J. Mol. Biol. 248, 361-373 (1995); (b) Milner-White, E.J., et al. J. Mol.Biol. 248, 374-384 (1995).6. A 4R electron-withdrawing group (EWG) brings the O i–1 or S i–1 donor and C i =O i acceptor closer; a4S EWG increases the distance between the donor and acceptor.7. Jackobsche, C.E., et al. J. Am. Chem. Soc. 132, 6651-6653 (2010).8. Bartlett, G.J., et al. Nat. Chem. Biol. 6, 615-620 (2010).9. Choudhary, A., et al. unpublished results.10. Lario, P.I., Vrielink, A. J. Am. Chem. Soc. 125, 12787-12794 (2003).11. Shoulders, M.D., Raines, R.T. Annu. Rev. Biochem. 78, 929-958 (2009), and references therein.12. Shoulders, M.D., et al. J. Am. Chem. Soc. 132, 10857-10865 (2010).13. Choudhary, A., et al. ACS Chem. Biol. 5, 655-657 (2010).3
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Mimicry Effect of the Neo-Epitope [Asn 641 (Glc)]FAN(635-655)with CSF114(Glc) Detecting Autoantibodies inMultiple SclerosisShashank Pandey 1,2 , Elisa Peroni 1,3 , Maria Claudia Alcaro 4 ,Fabio Rizzolo 1,2 , Mario Chelli 1,2 , Paolo Rovero 1,2,4 , Francesco Lolli 1,5 ,and Anna Maria Papini 1,2,31 Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico e Tecnologico,University of Florence, 50019, Sesto Fiorentino (FI), Italy; 2 Department of Chemistry andCNR ICCOM, Via della Lastruccia 3/13, University of Florence, I-50019, Sesto Fiorentino(FI), Italy; 3 Laboratoire SOSCO-EA4505, Universitè de Cergy-Pontoise, Neuville-sur-OiseF-95031, Cergy-Pontoise, France; 4 Toscana Biomarkers Srl, via Fiorentina 1, I-53100,Siena, Italy; 5 Department of Neurological Sciences & Azienda Ospedaliera Careggi,Viale Morgagni 34, University of Florence, I-50134, Firenze, Italy; 6 Department ofPharmaceutical Sciences Via Ugo Schiff University of Florence, I-50019,Sesto Fiorentino (FI), ItalyIntroductionMultiple sclerosis (MS) is an inflammatory demyelinating disease of the central nervoussystem (CNS) whose pathogenesis has not been yet elucidated, even if an autoimmunemechanism against myelin antigens is thought to contribute to its immunopathologicalmechanism. Anyway, the target antigens responsible for inflammation and demyelinationremain elusive. Different self-proteins have been investigated as potential targets for T or Bcells in MS [1-4]. We demonstrated for the first time, the possibility of using theglycosylated peptide CSF114(Glc) to identify specific autoantibodies in Multiple Sclerosispatients’ sera [5,6].We report herein, the mimicry effect of CSF114(Glc) with neo-epitope peptides andthe potential of this artificially N-glucosylated peptide sequence in identifying nativepeptides detecting autoantibodies.Results and DiscussionSome fragments of the nervous system proteins containing N-glycosylation consensus site(Asn-Xaa-Ser/Thr) were selected by primary as well as tertiary structure alignment ofCSF114(Glc) using SwissProt database.Selected fragments were peptides of Factor Associated with Neutral sphingomyelinaseactivation Asn 641 FAN(635-655); Oligodendrocyte Myelin glycoprotein Asn 192 OMgp(186-204) and Nogo receptor [Asn 179 ]NogoR(173-191), which displayed 8/21, 3/21, and 5/21residues homology with CSF114(Glc), respectively (Table 1).It was possible to synthesize peptide fragments only by microwave-assisted peptideand glycopeptide synthesis introducing Asn(Glc) at the requested position by the buildingblock approach using Fmoc-Asn(GlcOAc 4 )-OH. The neo-glycopeptides were analyzed inSP-ELISA on sera of clinically definite MS patients (Figure 1a) compared to Normal BloodDonors (data not shown).Table 1. Neo-peptide epitopesGlycosylated peptidesSequences[Asn 641 (Glc)]FAN(635-655) G I T V S R N G S S V F T T S Q D S T L K[Asn 192 (Glc)]OMgp(186-204) T L I N L T N L T H L Y L H N N K F T F I[Asn 179 (Glc)]NogoR(173-191) T F R D L G N L T H L F L H G N R I S S VCSF114(Glc) T P R V E R N G H S V F L A P Y G W M V K(N X T/S)=N-glycosylation consensus sequence4
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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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