Literature DB >> 27278825

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

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

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.

Entities:  

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

Year:  2016        PMID： 27278825     DOI： 10.1007/s13361-016-1427-8

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN： 1044-0305            Impact factor:   3.109


  22 in total

1.  Significant acceleration of 6 pi-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis.

Authors:  K Tanaka; H Mori; M Yamamoto; S Katsumura
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

2.  Atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry of Carotenoids.

Authors:  Richard B van Breemen; Linlin Dong; Natasa D Pajkovic
Journal:  Int J Mass Spectrom       Date:  2012-02-15       Impact factor: 1.986

3.  Structural characterization of drug-like compounds by ion mobility mass spectrometry: comparison of theoretical and experimentally derived nitrogen collision cross sections.

Authors:  Iain Campuzano; Matthew F Bush; Carol V Robinson; Claire Beaumont; Keith Richardson; Hyungjun Kim; Hugh I Kim
Journal:  Anal Chem       Date:  2011-12-27       Impact factor: 6.986

4.  Retinal shows its true colours: photoisomerization action spectra of mobility-selected isomers of the retinal protonated Schiff base.

Authors:  N J A Coughlan; B D Adamson; L Gamon; K Catani; E J Bieske
Journal:  Phys Chem Chem Phys       Date:  2015-08-17       Impact factor: 3.676

5.  Ion Mobility Unlocks the Photofragmentation Mechanism of Retinal Protonated Schiff Base.

Authors:  N J A Coughlan; B D Adamson; K J Catani; U Wille; E J Bieske
Journal:  J Phys Chem Lett       Date:  2014-09-04       Impact factor: 6.475

6.  Photoresponse of the protonated Schiff-base retinal chromophore in the gas phase.

Authors:  Y Toker; D B Rahbek; H V Kiefer; J Rajput; R Antoine; P Dugourd; S Brøndsted Nielsen; A V Bochenkova; L H Andersen
Journal:  Phys Chem Chem Phys       Date:  2013-12-07       Impact factor: 3.676

7.  Photoisomerization action spectrum of retinal protonated Schiff base in the gas phase.

Authors:  N J A Coughlan; K J Catani; B D Adamson; U Wille; E J Bieske
Journal:  J Chem Phys       Date:  2014-04-28       Impact factor: 3.488

8.  Electrocyclization reaction of higher conjugated polyenals: photochemical behaviors of retinal (vitamin A1 aldehyde) homologues.

Authors:  K Tsukida; M Ito; A Kodama
Journal:  J Nutr Sci Vitaminol (Tokyo)       Date:  1978       Impact factor: 2.000

9.  Isolation and characterization of a retinal pigment epithelial cell fluorophore: an all-trans-retinal dimer conjugate.

Authors:  Nathan E Fishkin; Janet R Sparrow; Rando Allikmets; Koji Nakanishi
Journal:  Proc Natl Acad Sci U S A       Date:  2005-05-03       Impact factor: 11.205

10.  The all-trans-retinal dimer series of lipofuscin pigments in retinal pigment epithelial cells in a recessive Stargardt disease model.

Authors:  So R Kim; Young P Jang; Steffen Jockusch; Nathan E Fishkin; Nicholas J Turro; Janet R Sparrow
Journal:  Proc Natl Acad Sci U S A       Date:  2007-11-28       Impact factor: 11.205
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