Complexation of L‐Lactate with Boronic Acids: A Solution and Holographic Analysis

Abstract

Boronic acids have been used as receptors for the detection of diols and alpha-hydroxy acids. The incorporation of 3-acrylamide phenyl boronic acid (3-APB) into a hydrogel generates a suitably responsive and fully reversible holographic sensor for L-lactate. However, it was also found that the use of 3-APB resulted in the sensor being responsive towards a number of other compounds containing two hydroxy groups. This report details the further investigation into the reaction between L-lactate and three boronic acid-based receptors, both in the holograms and in solution, in order to establish the mechanism of binding. A novel boronate receptor is proposed based on this understanding.

A near infrared holographic glucose sensor

“…2002) Furthermore, the conformational structures in other 11 BNMR pH-depression experiments with 3-acrylamidophenylboronic acid are in approximate agreement with findings in this work (Sartain, 2008;Xiaoping Yang et al, 2006).…”

Metabolic engineering of lactate dehydrogenase rescues mice from acidosis

“…The peak shifts obtained from these experiments correlated with the peak shifts obtained from the boron NMR of an ABA-lactate synthetic standard (isolated via preparative TLC). These data demonstrate that ABA specifically complexes with lactate and does not bind any of the metabolites normally present in serum and DMEM10.…”

“…ABA forms a bivalent complex with lactate and thereby decreases the intracellular lactate concentration, shifting the equilibrium towards the production of more lactate, resulting in the consumption of protons via hydrogenation of pyruvate. Importantly, ABA is specific for lactate over other metabolites such as glucose, because of its ortho-hydroxyl, which prevents it from binding cis-diols10. In addition, ABA also increases the NAD + /NADH ratio, which also has numerous therapeutic effects, such as protection against apoptosis and suppression of inflammation.…”

Progress in zeolite synthesis promotes advanced applications

“…The process of detection involves a change in the optical characteristics of the hologram caused by the interaction of the analyte with the support medium. The main effort in the development of holographic sensors for visual detection has been focused on reflection holographic sensors [72][73][74][75][76] and on optimization of the support medium to be analyte specific. The principle of operation of these holographic sensors [72][73][74][75][76] relies mainly on swelling/shrinking of the hologram support medium as a result of the exposure to the analyte and this leads to a visually observable change of the color of the light reflected by the hologram.…”