Interactions between boric acid derivatives and saccharides in aqueous media: Structures and stabilities of resulting esters

• Speciation of bor(on)ic and bor(on)ate esters depends on pKas and pH.
• Stability and selectivity depend largely on steric effects.
• Stability and selectivity can be increased by introduction of additional binding sites.
• Free glucose and fructose, glycated proteins (HSA hemoglobin), and bound and free sialic acid are good targets for B-based targeting vectors.

The general principles of interaction between bor(on)ic acids and sugars in aqueous media are discussed with a focus on the structural aspects that play a role with respect to the regioselectivity of the interactions and the stability of the resulting adducts. Preorganization and pKas appear to play important roles. Glucose and sialic acid will be demonstrated to be the promising targets for artificial B-based sensors. These sugars are important markers for diabetes and cancer, respectively.

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