Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water

Tom Carter, Tiddo Mooibroek, Patrick Stewart, Matthew Crump, Carmen Galan, Anthony Davis

Research output: Contribution to journalArticle (Academic Journal)

25 Citations (Scopus)
296 Downloads (Pure)

Abstract

Biomimetic carbohydrate receptors (“synthetic lectins”) have potential as agents for biological research and medicine. However, although effective strategies are available for “all-equatorial” carbohydrates (glucose, etc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report a new approach based on a pyrene platform with polar arches extending from aryl substituents. The receptors are compatible with axially substituted carbohydrates, and also feature two identical binding sites, thus mimicking the multivalency observed for natural lectins. A variant with negative charges forms 1:2 host/guest complexes with aminosugars, with K1>3000 m−1 for axially substituted mannosamine, whereas a positively charged version binds the important α-sialyl unit with K1≈1300 m−1.
Original languageEnglish
Pages (from-to)9311–9315
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number32
Early online date17 Jun 2016
DOIs
Publication statusPublished - 1 Aug 2016

Structured keywords

  • BCS and TECS CDTs

Keywords

  • carbohydrates
  • dendrimers
  • molecular recognition
  • receptors
  • supramolecular chemistry

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    Reworking of Novel tools for Glycoscience

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