Issue 30, 2012

New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity

Abstract

Synthetic lectins are molecules designed for the challenging task of biomimetic carbohydrate recognition in water. Previous work has explored a family of such systems based on bi/terphenyl units as hydrophobic surfaces and isophthalamide spacers to provide polar binding groups. Here we report a related receptor which employs a new spacer, 2,5-bis-(aminomethyl)-pyrrole, with an alternative (A-D-A) set of H-bonding valencies. The modified spacer leads to significant changes in binding selectivity, including a preference for glucose over all other tested substrates.

Graphical abstract: New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity

Supplementary files

Article information

Article type
Communication
Submitted
10 מאי 2012
Accepted
13 יונ 2012
First published
13 יונ 2012

Org. Biomol. Chem., 2012,10, 5760-5763

New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity

G. Joshi and A. P. Davis, Org. Biomol. Chem., 2012, 10, 5760 DOI: 10.1039/C2OB25900A

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