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

NJA Coughlan; MS Scholz; CS Hansen; AJ Trevitt; BD Adamson; EJ Bieske

Journal article

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

NJA Coughlan, MS Scholz, CS Hansen, AJ Trevitt, BD Adamson, EJ Bieske

Journal of the American Society for Mass Spectrometry | AMER CHEMICAL SOC | Published : 2016

DOI: 10.1007/s13361-016-1427-8

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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[Figure not available: see fulltext.]

University of Melbourne Researchers

Evan Bieske Author

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

This research was supported under the Australian Research Council's Discovery Project funding scheme (Project Numbers DP110100312 and DP120100100). The Australian Research Council is acknowledged for support for the Orbitrap mass spectrometer at UOW through LE120100059. The authors thank Professor Matthew Bush for providing a modified version of the Mobcal code with N<INF>2</INF> collision parameters described in ref. [28].