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

Gururaj Joshi; Anthony P. Davis

doi:10.1039/C2OB25900A

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Organic & Biomolecular Chemistry

Issue 30, 2012

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

Gururaj Joshi^a^b and Anthony P. Davis*^a

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School of Chemistry, University of Bristol, Cantock's Close, Bristol BS1 1TS, UK
E-mail: Anthony.Davis@bristol.ac.uk;
Fax: +44 (0) 117 9298611 ;
Tel: +44 (0) 117 9546334

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, USA

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

DOI: 10.1039/C2OB25900A
Received 10 May 2012, Accepted 13 Jun 2012
First published online 13 Jun 2012

This article is part of themed collection: Organic & Biomolecular Chemistry 10th Anniversary

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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.

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

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