mz8b00825_si_001.pdf (4.72 MB)
Double-Modified Glycopolymers from Thiolactones to Modulate Lectin Selectivity and Affinity
journal contribution
posted on 2018-12-06, 13:18 authored by Laura
E. Wilkins, Nezha Badi, Filip Du Prez, Matthew I. GibsonMultivalent glycomaterials
show high affinity toward lectins but
are often nonselective as they lack the precise 3-D presentation found
in native glycans. Here, thiolactone chemistry is exploited to enable
the synthesis of glycopolymers with both a primary binding (galactose)
and a variable secondary binding unit in close proximity to each other
on the linker. These polymers are used to target the Cholera toxin
B subunit, CTxB, inspired by its native branched glycan target, GM-1.
The secondary, nonbinding unit was shown to dramatically modulate
affinity and selectivity toward the Cholera toxin. These increasingly
complex glycopolymers, assembled using accessible chemistry, can help
breach the synthetic/biological divide to obtain future glycomimetics.
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Double-Modified GlycopolymersGM -1.proximitylackModulate Lectin Selectivityselectivitythiolactone chemistryaffinityfuture glycomimeticsCTxBbreachsynthesislinkerThiolactone3- D presentationCholera toxin B subunitCholera toxinbinding unitnonselectivegalactoseglycan targetAffinity Multivalent glycomaterials showlectinglycopolymer
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