“The paper is highly cited due to the remarkable growth in interest that this multidisciplinary field has attracted over the past few years, which is reflected in the increasing amount of work being published in this area.”

This paper is a focused review on boronic acid-based carbohydrate receptors. The paper is highly cited due to the remarkable growth in interest that this multidisciplinary field has attracted over the past few years, which is reflected in the increasing amount of work being published in this area.

This review describes advances in the field of boronic acid-based receptors for carbohydrates and covers early work while also focusing on recent developments in this expanding area. Our aim was to provide a useful tool, via this review article, for other researchers working on the design of carbohydrate receptors and chemosensors.

The chemistry of carbohydrates is of paramount importance to a wealth of biological functions within nature. By providing the building blocks for processes ranging from the production of metabolic energy through to tissue recognition, carbohydrates have found themselves to be the focus of a vast body of research aimed at understanding and mimicking their specific role and function at a cellular level.

Current enzymatic detection methods offer specificity for only a few carbohydrates; additionally, enzyme-based sensors are unstable under harsh conditions. Synthetic systems have been developed using hydrogen-bonding interactions for the purposes of recognition and binding of carbohydrates. However, in water, carbohydrates are heavily solvated and these hydrogen-bonding receptors find it hard to compete effectively with bulk water for low concentrations of carbohydrates.

Stable boronic acid-based carbohydrates receptors offer the possibility of creating designer carbohydrate sensors that can be selective and sensitive for any chosen carbohydrate in water. The recognition of carbohydrates by boronic acids has a unique place in supramolecular chemistry. The pair-wise interaction energy is large enough to allow single-point molecular recognition, and the primary interaction involves the reversible formation of a pair of covalent bonds—rather than non-covalent attractive forces.

Carbohydrates and related molecular species are involved in the metabolic pathways of living organisms, therefore, the detection of biologically important sugars (D-glucose, D-fructose, D-galactose, etc.), is vital in a variety of medicinal and industrial contexts. The recognition of D-glucose is of particular interest, since the breakdown of D-glucose transport in humans has been correlated with a number of diseases: renal glycosuria, cystic fibrosis, diabetes, and also cancer. Clear evidence exists that tight control of blood sugar levels in diabetics sharply reduces the risk of the debilitating long-term complications associated with this autoimmune disease. Industrial applications of carbohydrate detection range from the monitoring of fermenting processes to establishing the enantiomeric purity of synthetic drugs.