N-Acetyllactosamine is a common saccharide motif found in various biologically active glycans. This motif usually works as a backbone for additional modifications and thus significantly influences glycan conformational behavior and biological activity. In this work, we have investigated the type-2 N-acetyllactosamine scaffold using the complete series of its monodeoxyfluorinated analogs. These glycomimetics have been studied by molecular mechanics, quantum mechanics, X-ray crystallography, and various NMR techniques, which have provided a comprehensive and complete insight into the role of individual hydroxyl groups in the conformational behavior and lipophilicity of N-acetyllactosamine.

Centro de Investigaciones Biológicas Margarita Salas Ramiro de Maeztu 9 28040 Madrid Spain

CIBER de Enfermedades Respiratorias Avda Monforte de Lemos 3 5 28029 Madrid Spain

CICbioGUNE Basque Research and Technology Alliance Bizkaia Technology Park Building 800 48162 Derio Bizkaia Spain

Department of Inorganic Chemistry Faculty of Science Charles University Prague Hlavova 8 CZ 128 43 Praha 2 Czech Republic

Department of Organic and Inorganic Chemistry Faculty of Science and Technology University of the Basque Country EHU UPV 48940 Leioa Spain

Ikerbasque Basque Foundation for Science Plaza Euskadi 2 48013 Bilbao Bizkaia Spain

Institute of Chemical Process Fundamentals Czech Academy of Sciences Rozvojová 1 135 CZ 165 00 Praha 6 Czech Republic

Institute of Entomology Biology Centre of the Czech Academy of Sciences Branišovská 31 370 05 České Budějovice Czech Republic

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo náměstí 542 2 CZ 160 00 Praha 6 Czech Republic

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