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. 2019 Aug 7;17(29):7002-7006.
doi: 10.1039/c9ob01008d. Epub 2019 Jul 16.

Exploring the strength of a hydrogen bond as a function of steric environment using 1,2-azaborine ligands and engineered T4 lysozyme receptors

Yao Liu  1 , Shih-Yuan Liu  1
Affiliations

Exploring the strength of a hydrogen bond as a function of steric environment using 1,2-azaborine ligands and engineered T4 lysozyme receptors

Yao Liu et al. Org Biomol Chem. .

Abstract

A congeneric series of 1,2-azaborine ligands was used to study the relationship between the steric demand of the ligand and hydrogen bonding strength in the context of ligand-protein binding using engineered T4 lysozymes as the model biomacromolecules. The hydrogen bonding strength values were extracted from experimentally accessible binding free energies using the Double Mutant Cycle analysis. With the increasing steric demand, the NH…102Q hydrogen bonding interaction is weakened; however, this weakening of the hydrogen bonding interaction occurs in discrete steps rather than in an incremental fashion.

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Conflict of interest statement

Conflicts of interest

There are no conflicts of interest to declare.

Figures

Scheme 1
Scheme 1
Distinguishing features of the 1,2-azaborine motif.
Scheme 2
Scheme 2
This work: Evaluation of hydrogen bond strength as a function of steric environment via Double Mutant Cycle analysis.
Scheme 3
Scheme 3
A congeneric series of 1,2-azaborine ligands and its carbonaceous analogues.
Scheme 4
Scheme 4
The Double Mutant Cycle analysis for a congeneric ligand series.
Scheme 5
Scheme 5
General scheme and procedure for NHBnPr and NHBiPr.
See this image and copyright information in PMC

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