Pyrene-based synthetic lectins

Tiddo Mooibroek
University of Amsterdam

Carbohydrates are Nature’s most versatile class of molecules and fulfil various functions in the immune response system.1 Selective recognition of a particular (oligo-)saccharide could thus be exploited as an analytical means in biomedical research. For some illnesses, selective sensing could potentially be used as a diagnostic tool. However, binding carbohydrates selectively and in their natural environment (water) is challenging due to their hydromemetic hydroxyl exterior and the subtle differences between structural isomers. This challenge has been confronted using macrocyclic cages of a general ‘temple’ design that comprises complementary supramolecular synthons for interacting with a carbohydrate; polar ‘pillars’ for hydrogen bonding and hydrophobic aromatic surfaces for CH-π interactions. A remarkable selectivity has been demonstrated using biphenyl-based synthetic lectins with three or four pillars, although the binding affinities are generally moderate (Ka < 100 M-1). It was wondered what the effect would be of incorporating a larger condensed aromatic in these designs, leading to the pyrene analogues  discussed in this communication. These macrocycles proved to be very potent carbohydrate receptors with binding affinities in water up to 105 M-1. Several pyrene ‘hybrids’ will be discussed as well.

Tiddo Jonathan Mooibroek (12th March 1982) obtained his bachelor from the ‘Hogeschool Leiden’ (Cum Laude) in 2005, following both the organic and analytical chemistry tracks. He obtained his master degree in chemistry from the University of Leiden for which he was awarded the ‘Oosterhof award’ in 2007. In 2011 Tiddo defended his PhD thesis in industrial homogeneous catalysis and obtained a MA in philosophy both from the University of Leiden and the Free University of Amsterdam. He then moved to Bristol (UK), where he worked as a post-doctoral researcher on the development of pyrene-based receptors for carbohydrate recognition in aqueous solutions. In 2014 he became a Novo Nordisk ‘STAR’ research fellow in Bristol on a project to develop glucose-responsive insulin. Funded by a 2016 NWO VIDI grant, Tiddo is currently developing supramolecular catalysts for a one-step selective conversion of carbohydrates (at the University of Amsterdam). He also studies how unorthodox intermolecular interactions manifest themselves in solid state structures. At date, Tiddo has contributed to various international scientific meetings and is (co-)author of 46 publications in journals such as Nature Chemistry, Nature Communications, Angewandte Chemie and Journal of the American Chemical Society.

Dr. Tiddo Mooibroek

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