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For the \u03b1\u2010<jats:italic>O<\/jats:italic>\u2010GalNAc\u2010Ser derivative, the glycosidic linkage adopts a high\u2010energy conformation, barely populated in the free state. This unusual structure (also observed in an \u03b1\u2010<jats:italic>S<\/jats:italic>\u2010GalNAc\u2010Cys mimic) is stabilized by hydrogen bonds between the peptidic fragment and the sugar. The selection of a particular peptide structure by the antibody is thus propagated to the carbohydrate through carbohydrate\/peptide contacts, which force a change in the orientation of the sugar moiety. This seems to be unfeasible in the \u03b1\u2010<jats:italic>O<\/jats:italic>\u2010GalNAc\u2010Thr glycopeptide owing to the more limited flexibility of the side chain imposed by the methyl group. Our data demonstrate the non\u2010equivalence of Ser and Thr <jats:italic>O<\/jats:italic>\u2010glycosylation points in molecular recognition processes. These features provide insight into the occurrence in nature of the APDTRP epitope for anti\u2010MUC1 antibodies.<\/jats:p>","DOI":"10.1002\/anie.201502813","type":"journal-article","created":{"date-parts":[[2015,6,27]],"date-time":"2015-06-27T08:57:08Z","timestamp":1435395428000},"page":"9830-9834","source":"Crossref","is-referenced-by-count":79,"title":["Deciphering the Non\u2010Equivalence of Serine and Threonine <i>O<\/i>\u2010Glycosylation Points: Implications for Molecular Recognition of the Tn Antigen by an anti\u2010MUC1 Antibody"],"prefix":"10.1002","volume":"54","author":[{"given":"Nuria","family":"Mart\u00ednez\u2010S\u00e1ez","sequence":"first","affiliation":[]},{"given":"Jorge","family":"Castro\u2010L\u00f3pez","sequence":"additional","affiliation":[]},{"given":"Jessika","family":"Valero\u2010Gonz\u00e1lez","sequence":"additional","affiliation":[]},{"given":"David","family":"Madariaga","sequence":"additional","affiliation":[]},{"given":"Ismael","family":"Compa\u00f1\u00f3n","sequence":"additional","affiliation":[]},{"given":"V\u00edctor J.","family":"Somovilla","sequence":"additional","affiliation":[]},{"given":"M\u00edriam","family":"Salvad\u00f3","sequence":"additional","affiliation":[]},{"given":"Juan L.","family":"Asensio","sequence":"additional","affiliation":[]},{"given":"Jes\u00fas","family":"Jim\u00e9nez\u2010Barbero","sequence":"additional","affiliation":[]},{"given":"Alberto","family":"Avenoza","sequence":"additional","affiliation":[]},{"given":"Jes\u00fas H.","family":"Busto","sequence":"additional","affiliation":[]},{"given":"Gon\u00e7alo J. 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