{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T18:46:41Z","timestamp":1791226001859,"version":"4.1.0"},"reference-count":30,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2015,9,24]],"date-time":"2015-09-24T00:00:00Z","timestamp":1443052800000},"content-version":"vor","delay-in-days":23,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003056","name":"Ente Cassa di Risparmio di Firenze","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003056","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-09-CEXC-013-01"],"award-info":[{"award-number":["ANR-09-CEXC-013-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Fondation Pierre-Gilles de Gennes"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biopolymers"],"published-print":{"date-parts":[[2015,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Antibody detection in autoimmune disorders, such as multiple sclerosis (MS) and Rett syndrome (RTT) can be achieved more efficiently using synthetic peptides. The previously developed synthetic antigenic probe CSF114(Glc), a type I\u2032 \u03b2\u2010turn N\u2010glucosylated peptide structure, is able to recognize antibodies in MS and RTT patients\u2019 sera as a sign of immune system derangement. We report herein the design, synthesis, conformational analysis, and immunological evaluation of a collection of glycopeptide analogs of CSF114(Glc) to characterize the specific role of secondary structures in MS and RTT antibody recognition. Therefore, we synthesized a series of linear and cyclic short glucosylated sequences, mimicking different \u03b2\u2010turn conformations, which were evaluated in inhibition enzyme\u2010linked immunosorbent assays (ELISA). Calculated IC<jats:sub>50<\/jats:sub> ranking analysis allowed the selection of the candidate octapeptide containing two (S)\u22122\u2010amino\u20104\u2010pentynoic acid (L\u2010Pra) residues Ac\u2010Pra\u2010RRN(Glc)GHT\u2010Pra\u2010NH<jats:sub>2<\/jats:sub>, with an IC<jats:sub>50<\/jats:sub> in the nanomolar range. This peptide was adequately modified for solid\u2010phase ELISA (SP\u2010ELISA) and surface plasmon resonance (SPR) experiments. Pra\u2010RRN(Glc)GHT\u2010Pra\u2010NH<jats:sub>2<\/jats:sub> peptide was modified with an alkyl chain linked to the N\u2010terminus, favoring immobilization on solid phase in SP\u2010ELISA and differentiating IgG antibody recognition between patients and healthy blood donors with a high specificity. However, this peptide displayed a loss in IgM specificity and sensitivity. Moreover, an analog was obtained after modification of the octapeptide candidate Ac\u2010Pra\u2010RRN(Glc)GHT\u2010Pra\u2010NH<jats:sub>2<\/jats:sub> to favor immobilization on SPR sensor chips. SPR technology allowed us to determine its affinity (K<jats:sub>D<\/jats:sub>\u2009=\u200916.4 nM), 2.3 times lower than the affinity of the original glucopeptide CSF114(Glc) (K<jats:sub>D<\/jats:sub>\u2009=\u20097.1 nM). \u00a9 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 560\u2013576, 2015.<\/jats:p>","DOI":"10.1002\/bip.22677","type":"journal-article","created":{"date-parts":[[2015,5,13]],"date-time":"2015-05-13T22:29:18Z","timestamp":1431556158000},"page":"560-576","source":"Crossref","is-referenced-by-count":22,"title":["Antibody Recognition in multiple sclerosis and rett syndrome using a collection of linear and cyclic <i>N<\/i>\u2010glucosylated antigenic probes"],"prefix":"10.1002","volume":"104","author":[{"given":"Feliciana","family":"Real Fern\u00e1ndez","sequence":"first","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"Department of Neurosciences, Psychology, Drug Research and Child Health, Section of Pharmaceutical Sciences and Nutraceutics University of Florence Via Ugo Schiff 6, 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Margherita","family":"Di Pisa","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giada","family":"Rossi","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"Department of Neurosciences, Psychology, Drug Research and Child Health, Section of Pharmaceutical Sciences and Nutraceutics University of Florence Via Ugo Schiff 6, 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicolas","family":"Auberger","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olivier","family":"Lequin","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maud","family":"Larregola","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"PeptLab@UCP Platform and Laboratory of Chemical Biology EA4505 University of Cergy\u2010Pontoise 5 Mail Gay Lussac 95031 Cergy\u2010Pontoise Cedex France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amina","family":"Benchohra","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"Department of Chemistry \u2018Ugo Schiff\u2019 University of Florence Via della Lastruccia 13 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christelle","family":"Mansuy","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gerard","family":"Chassaing","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesco","family":"Lolli","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"Dipartimento di Scienze Biomediche Sperimentali e Cliniche University of Florence Viale Morgagni 50 50134 Firenze Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joussef","family":"Hayek","sequence":"additional","affiliation":[{"name":"Child Neuropsychiatry Unit Azienda Ospedaliera Universitaria Senese (AOUS) 53100 Siena Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Solange","family":"Lavielle","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paolo","family":"Rovero","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"Department of Neurosciences, Psychology, Drug Research and Child Health, Section of Pharmaceutical Sciences and Nutraceutics University of Florence Via Ugo Schiff 6, 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean\u2010Maurice","family":"Mallet","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie \u00c9cole Normale Sup\u00e9rieure\u2014PSL Research University 24 rue Lhomond, Sorbonne Universit\u00e9s, UPMC Univ Paris 06, LBM, 4 place Jussieu, CNRS, UMR 7203 LBM 75005 Paris France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna Maria","family":"Papini","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry and Biology, PeptLab (http:\/\/www.peptlab.eu)"},{"name":"PeptLab@UCP Platform and Laboratory of Chemical Biology EA4505 University of Cergy\u2010Pontoise 5 Mail Gay Lussac 95031 Cergy\u2010Pontoise Cedex France"},{"name":"Department of Chemistry \u2018Ugo Schiff\u2019 University of Florence Via della Lastruccia 13 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,9,24]]},"reference":[{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.1373\/clinchem.2005.051532"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1471-4906(01)01976-7"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/psc.1166"},{"key":"e_1_2_5_5_1","first-page":"11","volume":"27","author":"Alcaro M. C.","year":"2009","journal-title":"Chim Oggi"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/1529-0131(200001)43:1<155::AID-ANR20>3.0.CO;2-3"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2249.2011.04378.x"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0503178102"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jneuroim.2005.05.016"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.1155\/2014\/260973"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm060117j"},{"key":"e_1_2_5_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm800391y"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1074\/mcp.M112.017087"},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm301031r"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1089\/jmf.2014.0028"},{"key":"e_1_2_5_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo011148j"},{"key":"e_1_2_5_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo800142s"},{"key":"e_1_2_5_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/psc.1382"},{"key":"e_1_2_5_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501027w"},{"key":"e_1_2_5_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.10.026"},{"key":"e_1_2_5_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/bip.21456"},{"key":"e_1_2_5_22_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00127968"},{"key":"e_1_2_5_23_1","volume":"701","author":"Vilhelmsen M. 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