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Mechanical confinement of glycans generates localized plasmonic hot spots, enabling highly reproducible and structurally informative vibrational spectra. The system resolves subtle structural differences such as \u03b2(1\u21923) vs. \u03b2(1\u21924) glycosidic linkages, and allows semi\u2010quantitative estimation of chain length based on H\u2013C\u2013H deformation signatures. The azido tag provides an internal reference, supporting signal normalization from trace sample volumes. The platform also tracks enzymatic glycosylation reactions in real time, including the emergence of \u03b11\u21922 fucosylation linkages. This approach distinguishes single\u2010bond differences and monitors biosynthetic progression with high molecular specificity. 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