Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins
Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins
Three all-trans retinals containing multiple 13C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsin and channelrhodopsin. The synthetic approaches allowed specific introduction of 13C labels in ring substituents and at different positions in the polyene chain to probe structural features such as ring orientation and interaction of the chromophore with the protein in the ground state and in photointermediates. [10-18-13C9]-All-trans-retinal (1b), [12,15-13C2]-all-trans-retinal (1c), and [14,15-13C2]-all-trans-retinal (1d) were synthesized in in 12, 8, and 7 linear steps from ethyl 2-oxocyclohexanecarboxylate (5) or β-ionone (4), respectively.
1-12
Leeder, Alexander J.
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Brown, Lynda J.
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Becker-Baldus, Johanna
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Mehler, Michaela
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Glaubitz, Clemens
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Brown, Richard C.D.
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Leeder, Alexander J.
82f20bdd-9d92-47b8-8720-6f5c66db4be7
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Becker-Baldus, Johanna
6563d44b-d7aa-4e93-b7c2-57b95f8a0f1d
Mehler, Michaela
1542ef93-5644-4dbf-84ff-c1980fdb40d6
Glaubitz, Clemens
99f5e847-e6fd-4783-bc60-054bf0e15661
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Leeder, Alexander J., Brown, Lynda J., Becker-Baldus, Johanna, Mehler, Michaela, Glaubitz, Clemens and Brown, Richard C.D.
(2018)
Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins.
Journal of Labelled Compounds and Radiopharmaceuticals, .
(doi:10.1002/jlcr.3576).
Abstract
Three all-trans retinals containing multiple 13C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsin and channelrhodopsin. The synthetic approaches allowed specific introduction of 13C labels in ring substituents and at different positions in the polyene chain to probe structural features such as ring orientation and interaction of the chromophore with the protein in the ground state and in photointermediates. [10-18-13C9]-All-trans-retinal (1b), [12,15-13C2]-all-trans-retinal (1c), and [14,15-13C2]-all-trans-retinal (1d) were synthesized in in 12, 8, and 7 linear steps from ethyl 2-oxocyclohexanecarboxylate (5) or β-ionone (4), respectively.
Text
Retinal (J Labelled Compd)
- Accepted Manuscript
More information
Accepted/In Press date: 17 October 2017
e-pub ahead of print date: 2 February 2018
Identifiers
Local EPrints ID: 415124
URI: http://eprints.soton.ac.uk/id/eprint/415124
ISSN: 0362-4803
PURE UUID: 0114695f-c7c1-4f86-af94-883a0e2be2ee
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Date deposited: 31 Oct 2017 17:30
Last modified: 16 Mar 2024 05:51
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Contributors
Author:
Alexander J. Leeder
Author:
Johanna Becker-Baldus
Author:
Michaela Mehler
Author:
Clemens Glaubitz
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