SupraBank - High Fidelity Kinetic Self-Sorting in Multi-Component Systems Based on Guests with Multiple Binding Epitopes

DOI:: https://doi.org/10.34804/supra.20210928343
Title:: High Fidelity Kinetic Self-Sorting in Multi-Component Systems Based on Guests with Multiple Binding Epitopes

Description:: The molecular recognition platforms of natural systems often possess multiple binding epitopes, each of which has programmed functional consequences. We report the dynamic behavior of a system comprising CB[6], CB[7], and guests cyclohexanediammonium (1) and adamantanealkylammonium (2) that we refer to as a two-faced guest because it contains two distinct binding epitopes. We find that the presence of the two-faced guestjust as is observed for protein targeting in vivodictates the kinetic pathway that the system follows toward equilibrium. The influence of two-faced guest structure, cation concentration, cation identity, and individual rate and equilibrium constants on the behavior of the system was explored by a combination of experiment and simulation. Deconstruction of this system led to the discovery of an anomalous host−guest complex (CB[6]·1) whose dissociation rate constant (kout = 8.5 × 10-10 s-1) is ≈100-fold slower than the widely used avidin·biotin affinity pair. This result, in combination with the analysis of previous systems which uncovered extraordinarily tight binding events (Ka ≥ 1012 M-1), highlights the inherent potential of pursuing a systems approach toward supramolecular chemistry.

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Citation:	L. Isaacs, P. Y. Zavalij, P. Mukhopadhyay, SupraBank 2024, High Fidelity Kinetic Self-Sorting in Multi-Component Systems Based on Guests with Multiple Binding Epitopes (dataset). https://doi.org/10.34804/supra.20210928343
Link:	https://doi.org/10.34804/supra.20210928343
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Citation:	P. Mukhopadhyay, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2006, 128, 14093–14102.
Link:	https://doi.org/10.1021/ja063390j
Export:	BibTex \| RIS \| EndNote \|