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Issue 30, 2012
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New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity

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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

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Publication details

The article was received on 10 May 2012, accepted on 13 Jun 2012, published on 13 Jun 2012 and first published online on 13 Jun 2012


Article type: Communication
DOI: 10.1039/C2OB25900A
Citation: Org. Biomol. Chem., 2012,10, 5760-5763
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    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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