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Molecules 2010, 15(3), 1825-1872; doi:10.3390/molecules15031825

Synthesis and Use of Stable Isotope Enriched Retinals in the Field of Vitamin A

Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA, Leiden, The Netherlands
* Author to whom correspondence should be addressed.
Received: 15 January 2010 / Revised: 18 February 2010 / Accepted: 2 March 2010 / Published: 15 March 2010
(This article belongs to the Special Issue Vitamins)
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The role of vitamin A and its metabolites in the life processes starting with the historical background and its up to date information is discussed in the introduction. Also the role of 11Z-retinal in vision and retinoic acid in the biological processes is elucidated. The essential role of isotopically enriched systems in the progress of vision research, nutrition research etc. is discussed. In part B industrial commercial syntheses of vitamin A by the two leading companies Hoffmann-La Roche (now DSM) and BASF are discussed. The knowledge obtained via these pioneering syntheses has been essential for the further synthetic efforts in vitamin A field by other scientific groups. The rest of the paper is devoted to the synthetic efforts of the Leiden group that gives an access to the preparation of site directed high level isotope enrichment in retinals. First the synthesis of the retinals with deuterium incorporation in the conjugated side chain is reviewed. Then, 13C-labeled retinals are discussed. This is followed by the discussion of a convergent synthetic scheme that allows a rational access to prepare any isotopomer of retinals. The schemes that provide access to prepare any possible isotope enriched chemically modified systems are discussed. Finally, nor-retinals and bridged retinals that give access to a whole (as yet incomplete) library of possible isotopomers are reviewed.
Keywords: wittig reaction; nitrile chemistry; retinals; deuterium; 13C-incorporation wittig reaction; nitrile chemistry; retinals; deuterium; 13C-incorporation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Dawadi, P.B.; Lugtenburg, J. Synthesis and Use of Stable Isotope Enriched Retinals in the Field of Vitamin A. Molecules 2010, 15, 1825-1872.

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