Hydrogen Bonding Parameters by Rapid Colorimetric Assessment: Evaluation of Structural Components Found in Biological Ligands and Organocatalysts

Author:

Roenfanz Hanna F.1ORCID,Paniak Thomas J.1ORCID,Berlin Cameron B.1,Tran Van1,Francisco Karol R.2ORCID,Lassalas Pierrik1ORCID,Devas Anisha1,Landes Olivia1,Rosenberger Avalon1,Rotella Madeline E.1ORCID,Ballatore Carlo3ORCID,Kozlowski Marisa C.1ORCID

Affiliation:

1. Department of Chemistry University of Pennsylvania 231 South 34th Street Philadelphia PA 19104 USA

2. Department of Chemistry and Biochemistry University of California San Diego 9500 Gilman Drive La Jolla CA 92093 USA

3. Skaggs School of Pharmacy and Pharmaceutical Sciences University of California San Diego 9500 Gilman Drive La Jolla CA 92093 USA

Abstract

AbstractHydrogen bonding is a key molecular interaction in biological processes, drug delivery, and catalysis. This report describes a high throughput UV‐Vis spectroscopic method to measure hydrogen bonding capacity using a pyrazinone sensor. This colormetric sensor reversibly binds to a hydrogen bond donor, resulting in a blue shift as additional equivalents of donor are added. Titration with excess equivalents of donor is used to determine the binding coefficient, ln(Keq). Over 100 titrations were performed for a variety of biologically relevant compounds. This data enabled development a multiple linear regression model that is capable of predicting 95 % of ln(Keq) values within 1 unit, allowing for the estimation of hydrogen bonding affinity from a single measurement. To show the effectiveness of the single point measurements, hydrogen bond strengths were obtained for a set of carboxylic acid bioisosteres. The values from the single point measurements were validated with full titrations.

Funder

National Institutes of Health

National Science Foundation

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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