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Syntheses of 13C2-labelled 11Z-retinals

Syntheses of 13C2-labelled 11Z-retinals
Syntheses of 13C2-labelled 11Z-retinals
To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann–Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of ?-ionone with labelled triethyl phosphonoacetate
0040-4020
8404-8410
McLean, Neville J.
442ed7d5-0f16-4c0f-8fed-c4437aa800cc
Gansmuller, Axel
239d731b-d3cb-4c2f-8c9e-ddb1e195c73f
Concistre, Maria
ec95c9d4-ecb8-4c28-a464-8c3adba9e86d
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Levitt, Malcom H.
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
McLean, Neville J.
442ed7d5-0f16-4c0f-8fed-c4437aa800cc
Gansmuller, Axel
239d731b-d3cb-4c2f-8c9e-ddb1e195c73f
Concistre, Maria
ec95c9d4-ecb8-4c28-a464-8c3adba9e86d
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Levitt, Malcom H.
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

McLean, Neville J., Gansmuller, Axel, Concistre, Maria, Brown, Lynda J., Levitt, Malcom H. and Brown, Richard C.D. (2011) Syntheses of 13C2-labelled 11Z-retinals. Tetrahedron, 67 (43), 8404-8410. (doi:10.1016/j.tet.2011.07.092).

Record type: Article

Abstract

To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann–Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of ?-ionone with labelled triethyl phosphonoacetate

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e-pub ahead of print date: 22 August 2011
Published date: 28 October 2011
Organisations: Chemistry
Learn more about Chemistry research

Identifiers

Local EPrints ID: 337190
URI: http://eprints.soton.ac.uk/id/eprint/337190
DOI: doi:10.1016/j.tet.2011.07.092
ISSN: 0040-4020
PURE UUID: 5129408b-44f3-47d4-8ad2-a0008f040a3f
ORCID for Maria Concistre: ORCID iD orcid.org/0000-0001-7111-0782
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Malcom H. Levitt: ORCID iD orcid.org/0000-0001-9878-1180
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 20 Apr 2012 09:12
Last modified: 15 Mar 2024 03:32

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Contributors

Author: Neville J. McLean
Author: Axel Gansmuller
Author: Maria Concistre ORCID iD
Author: Lynda J. Brown ORCID iD
Author: Malcom H. Levitt ORCID iD
Author: Richard C.D. Brown ORCID iD

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