Title

Trans-2-(1,2,3-triazolyl)-cyclohexanols as Potential pHTriggered Molecular Switches

Poster Number

22

Lead Author Major

Biochemistry

Format

Poster Presentation

Faculty Mentor Name

Vyacheslav Samoshin

Faculty Mentor Department

Chemistry

Abstract/Artist Statement

Conformational molecular switches are molecular systems that reversibly change the relative orientation of their parts under external stimulus. They play a central role in the design of molecular machinery, controllable compounds and intelligent materials for possible use in many applications, including drug release, new sensor techniques or information storage and transmission. In particular, the trans-2- aminocyclohexanol moiety was used to construct the conformationally controlled crown-ethers and podands, and the pH-sensitive components of liposomes for targeted drug delivery. To further expand the variety of potential pHtriggers, we explored a new type of conformational switch based on trans-2-(1,2,3- triazolyl)-cyclohexanol. A series of these compounds was synthesized by a “click-reaction” of bis-ethoxycarbonyl-trans-2- azidocyclohexanol with substituted alkynes. This approach allows a broad variation of target structures. Select triazolyl compounds were also synthesized with various blocking groups on oxygen to limit premature hydrogen bonding before pH change. The conformational equilibrium and its pH-induced change were studied by 1H-NMR in several solvents. The position of equilibrium depends on the substituents at triazolyl cycle and on the solvent. However, the desired pH-sensitivity is limited by the initial bias of equilibrium towards the conformer with diequatorial triazolyl and oxy groups.

Location

DeRosa University Center, Ballroom

Start Date

25-4-2015 10:00 AM

End Date

25-4-2015 12:00 PM

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Apr 25th, 10:00 AM Apr 25th, 12:00 PM

Trans-2-(1,2,3-triazolyl)-cyclohexanols as Potential pHTriggered Molecular Switches

DeRosa University Center, Ballroom

Conformational molecular switches are molecular systems that reversibly change the relative orientation of their parts under external stimulus. They play a central role in the design of molecular machinery, controllable compounds and intelligent materials for possible use in many applications, including drug release, new sensor techniques or information storage and transmission. In particular, the trans-2- aminocyclohexanol moiety was used to construct the conformationally controlled crown-ethers and podands, and the pH-sensitive components of liposomes for targeted drug delivery. To further expand the variety of potential pHtriggers, we explored a new type of conformational switch based on trans-2-(1,2,3- triazolyl)-cyclohexanol. A series of these compounds was synthesized by a “click-reaction” of bis-ethoxycarbonyl-trans-2- azidocyclohexanol with substituted alkynes. This approach allows a broad variation of target structures. Select triazolyl compounds were also synthesized with various blocking groups on oxygen to limit premature hydrogen bonding before pH change. The conformational equilibrium and its pH-induced change were studied by 1H-NMR in several solvents. The position of equilibrium depends on the substituents at triazolyl cycle and on the solvent. However, the desired pH-sensitivity is limited by the initial bias of equilibrium towards the conformer with diequatorial triazolyl and oxy groups.