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

Gururaj Joshi; Anthony P. Davis

doi:10.1039/C2OB25900A

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

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

* Corresponding authors

^a 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

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

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.

Supplementary files

Publication details

The article was received on 10 May 2012, accepted on 13 Jun 2012 and first published 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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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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