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In this study we focused our attention on the trisaccharide human natural killer cell\u20101 (HNK\u20101), considered the antigenic determinant of myelin\u2010associated glycoprotein and the target of clinically relevant auto\u2010antibodies in autoimmune neurological disorders such as IgM monoclonal gammopathy and demyelinating polyneuropathy. We describe a structure\u2013activity relationship study based on surface plasmon resonance binding affinities aimed at the optimization of a peptide that mimics the HNK\u20101 minimal epitope. We developed a cyclic heptapeptide that shows an affinity of 1.09\u00d710<jats:sup>\u22127<\/jats:sup>\u2009<jats:sc>m<\/jats:sc> for a commercial anti\u2010HNK1 mouse monoclonal antibody. Detailed conformational analysis gave possible explanations for the good affinity displayed by this novel analogue, which was subsequently used as an immunological probe. However, preliminary screening indicates that patients\u2032 sera do not specifically recognize this peptide, showing that murine monoclonal antibodies cannot be used as a guide to select immunological probes for the detection of clinically relevant human auto\u2010antibodies.<\/jats:p>","DOI":"10.1002\/cmdc.201700042","type":"journal-article","created":{"date-parts":[[2017,4,12]],"date-time":"2017-04-12T13:14:45Z","timestamp":1492002885000},"page":"751-759","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Structure\u2013Activity Relationship Studies, SPR Affinity Characterization, and Conformational Analysis of Peptides That Mimic the HNK\u20101 Carbohydrate Epitope"],"prefix":"10.1002","volume":"12","author":[{"given":"Matthaia","family":"Ieronymaki","sequence":"first","affiliation":[{"name":"Laboratory of Peptide and Protein Chemistry and Biology PeptLab  Via della Lastruccia 13 50019 Sesto Fiorentino Italy"},{"name":"Department of Chemistry \u201cUgo Schiff\u201d University of Florence  Via della Lastruccia 13 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9908-5996","authenticated-orcid":false,"given":"Francesca","family":"Nuti","sequence":"additional","affiliation":[{"name":"Laboratory of Peptide and Protein Chemistry and Biology PeptLab  Via della Lastruccia 13 50019 Sesto Fiorentino Italy"},{"name":"Department of Chemistry \u201cUgo Schiff\u201d University of Florence  Via della Lastruccia 13 50019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diego","family":"Brancaccio","sequence":"additional","affiliation":[{"name":"Department of Pharmacy University of Naples \u201cFederico II\u201d  Via D. 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