The development of macrocyclic hosts for encapsulation of anions, particularly oxo anions such such as sulfate, phosphates, and carboxylates, has been an avid area of research. However, macrocycles are also capable of binding more complex oxo anions such as a highly phosphorylated biomolecule known as phytate, <i>myo</i>-inositol-1,2,3,4,5,6-hexakisphosphate. While having numerous roles in plant metabolism, phytate has an adverse effect on sequestering nutrients, including metal ions important in environmental and agricultural chemistry. The large number of phosphate groups leads to a wide range of charges - from -1 to -12, making this a captivating target for exploration of its complex chemistry. Moreover, structural implications of its conformation changes from 1a5e to 5a1e depending on the pH have been the subject of much interest. The crystallographic evidence of capture of a single anion of phytate within a simple sandwich host-guest complex using two 36-membered macrocycles as host will be described. The combination of crystallographic findings along with NMR spectroscopy has aided our understanding about intermolecular and intramolecular interactions of phytate. This presentation will highlight our recent results on unravelling the structural complexities of phytate.

Tunable macrocyclic hosts for phytate and more complex anions

ACS Spring Meeting 2021

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