Photo and Collision Induced Isomerization of a Cyclic Retinal Derivative: An Ion Mobility Study

Neville J A Coughlan; Michael S Scholz; Christopher S Hansen; Adam J Trevitt; Brian D Adamson; Evan J Bieske

doi:10.1007/s13361-016-1427-8

Photo and Collision Induced Isomerization of a Cyclic Retinal Derivative: An Ion Mobility Study

J Am Soc Mass Spectrom. 2016 Sep;27(9):1483-90. doi: 10.1007/s13361-016-1427-8. Epub 2016 Jun 8.

Authors

Neville J A Coughlan¹, Michael S Scholz¹, Christopher S Hansen², Adam J Trevitt², Brian D Adamson¹, Evan J Bieske³

Affiliations

¹ School of Chemistry, University of Melbourne, Melbourne, Australia.
² School of Chemistry, University of Wollongong, Wollongong, Australia.
³ School of Chemistry, University of Melbourne, Melbourne, Australia. evanjb@unimelb.edu.au.

PMID: 27278825
DOI: 10.1007/s13361-016-1427-8

Abstract

A cationic degradation product, formed in solution from retinal Schiff base (RSB), is examined in the gas phase using ion mobility spectrometry, photoisomerization action spectroscopy, and collision induced dissociation (CID). The degradation product is found to be N-n-butyl-2-(β-ionylidene)-4-methylpyridinium (BIP) produced through 6π electrocyclization of RSB followed by protonation and loss of dihydrogen. Ion mobility measurements show that BIP exists as trans and cis isomers that can be interconverted through buffer gas collisions and by exposure to light, with a maximum response at λ = 420 nm.Graphical Abstract.

Keywords: Collision induced isomerization; Ion mobility; Ion spectroscopy; Photoisomerization; Retinal.

Publication types

Research Support, Non-U.S. Gov't