Substituent Effects in Synthetic Lectins - Exploring the Role of CH-pi Interactions in Carbohydrate Recognition

Nicholas P. Barwell, Anthony P. Davis

Research output: Contribution to journalArticle (Academic Journal)

41 Citations (Scopus)

Abstract

Contacts between aromatic surfaces and saccharide CH groups are common motifs in natural carbohydrate recognition. These CH-pi interactions are modeled in "synthetic lectins" which employ oligophenyl units as apolar surfaces. Here we report the synthesis and study of new synthetic lectins with fluoro- and hydroxy-substituted biphenyl units, designed to explore the role of pi-electron density in carbohydrate CH-pi interactions. We find evidence that recognition can be moderated through electronic effects but that other factors such as cavity hydration are also important and sometimes predominant in determining binding strengths.

Original languageEnglish
Pages (from-to)6548-6557
Number of pages10
JournalJournal of Organic Chemistry
Volume76
Issue number16
DOIs
Publication statusPublished - 19 Aug 2011

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