We
present a synthetic approach toward soft, glycooligomer-functionalized
microgel particles mimicking carbohydrate presenting cell surfaces
and analyze their specific binding to a model lectin (Concanavalin
A, ConA). Focusing on multivalent presentation, a series of sequence-controlled
glycooligomers with varying spacing and number of mannose units was
synthesized and analyzed for the resulting glycooligomer–ConA
affinity. Both direct binding and inhibition studies show a higher
affinity with increasing the number of sugar moieties, but they level
off for higher valent systems, indicating steric hindrance. Furthermore,
the results suggest that increasing the scaffold length tends to decrease
binding due to entropic repulsion, which could be compensated by larger
scaffolds able to address multiple ConA binding sites. These findings
were consistent in all assays (adhesion, fluorescence, and ITC) regardless
of binding partner immobilization, demonstrating that flexible ligands
exert similar binding modes in solution and when attached to polymer
networks, which is relevant for designing glyco-functionalized materials
