Title

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches

Poster Number

6

Lead Author Affiliation

PhD, Pharmaceutical and Chemical Sciences; Chemical Synthesis, Drug Discovery and Design

Lead Author Status

Doctoral Student

Second Author Affiliation

Department of Chemistry

Second Author Status

Faculty

Introduction

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur.

Purpose

Exploring other nitrogen linked-cyclohexanol derivatives, like triazoles, could potentially give new models for conformational switches. The triazole substituent is unique because of the numerous attachments that can be linked to the alkyne before synthesis.

Method

Conformational equilibria of the triazolyl-cyclohexanol derivatives were analyzed by 1H NMR. The coupling width of the signal for the hydrogen, adjacent to the carbon on which the triazole ring is attached, was measured and compared to standard models that have their substituents in either the axial or equatorial position.

Results

The triazolyl substituent was shown to have a substantial conformational energy and to always shift the equilibrium toward the conformation, in which it occupies an equatorial position.

Significance

Triazolyl-cyclohexanols could be used as conformational locks in models that prefer to occupy the equatorial position.

Location

DUC Ballroom A&B

Format

Poster Presentation

Poster Session

Afternoon

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Apr 29th, 1:00 PM Apr 29th, 3:00 PM

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential conformational switches

DUC Ballroom A&B

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH range in which a switch can occur.