Cooperative Multipoint
Recognition of Sialic Acid
by Benzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors
Posted on 2020-06-18 - 06:44
Sialic acid recognition remains an
interesting and challenging
target in molecular receptor design. Herein, we report a series of
benzoboroxole-based receptors in which cationic hydrogen-bond donors
have been introduced and shown to promote multipoint sialic acid recognition.
One striking feature revealed by these receptors is that the carboxylate
sialic acid residue is the primary binding determinant for recognition
by benzoboroxole, in which the presence of charge-reinforced hydrogen
bonds results in enhanced selectivity for sialic acid over other carbohydrates
and a 4.5-fold increase in affinity. These findings open up wide possibilities
for benzoboroxole-based receptors use in life science research, biotechnology,
and diagnostics.
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Di Pasquale, Alice; Tommasone, Stefano; Xu, Lili; Ma, Jing; Mendes, Paula M. (2020). Cooperative Multipoint
Recognition of Sialic Acid
by Benzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.0c00173
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AUTHORS (5)
AD
Alice Di Pasquale
ST
Stefano Tommasone
LX
Lili Xu
JM
Jing Ma
PM
Paula M. Mendes
KEYWORDS
multipoint sialic acid recognitionbenzoboroxole-based receptorsreceptor designCooperative Multipoint Recognitioncarboxylate sialic acid residuecharge-reinforced hydrogen bonds resultscationic hydrogen-bond donorsBenzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors Sialic acid recognitionbinding determinantlife science researchsialic acidbenzoboroxole-based receptors use