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Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions.
Acta Biochim Pol. 2012; 59(1):11-6.AB

Abstract

Carotenoids and their metabolites are essential factors for the maintenance of important life processes such as photosynthesis. Animals cannot synthesize carotenoids de novo, they must obtain them via their food. In order to make intensive animal husbandry possible and maintain human and animal health synthetic nature identical carotenoids are presently commercially available at the multi-tonnes scale per year. Synthetically accessible (13)C enriched carotenoids are essential to apply isotope sensitive techniques to obtain information at the atomic level without perturbation about the role of carotenoids in photosynthesis, nutrition, vision, animal development, etc. Simple highly (13)C enriched C(1), C(2) and C(3) building blocks are commercially available via 99% (13)CO. The synthetic routes for the preparation of the (13)C enriched building blocks starting from the commercially available systems are discussed first. Then, how these building blocks are used for the synthesis of the various (13)C enriched carotenoids and apocarotenoids are reviewed next. The synthetic Schemes that resulted in (13)C enriched β-carotene, spheroidene, β-cryptoxanthin, canthaxanthin, astaxanthin, (3R,3'R)-zeaxanthin and (3R,3'R,6'R)-lutein are described. The Schemes that are reviewed can also be used to synthetically access any carotenoid and apocarotenoid in any (13)C isotopically enriched form up to the unitarily enriched form.

Authors+Show Affiliations

Leiden Institute of Chemistry, Leiden University, The Netherland. lugtenbu@chem.leidenuniv.nlNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22428113

Citation

Lugtenburg, Johan, and Prativa B S. Dawadi. "Synthesis of Highly 13C Enriched Carotenoids: Access to Carotenoids Enriched With 13C at Any Position and Combination of Positions." Acta Biochimica Polonica, vol. 59, no. 1, 2012, pp. 11-6.
Lugtenburg J, Dawadi PB. Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions. Acta Biochim Pol. 2012;59(1):11-6.
Lugtenburg, J., & Dawadi, P. B. (2012). Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions. Acta Biochimica Polonica, 59(1), 11-6.
Lugtenburg J, Dawadi PB. Synthesis of Highly 13C Enriched Carotenoids: Access to Carotenoids Enriched With 13C at Any Position and Combination of Positions. Acta Biochim Pol. 2012;59(1):11-6. PubMed PMID: 22428113.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions. AU - Lugtenburg,Johan, AU - Dawadi,Prativa B S, Y1 - 2012/03/17/ PY - 2011/09/28/received PY - 2012/03/01/accepted PY - 2012/3/20/entrez PY - 2012/3/20/pubmed PY - 2012/7/24/medline SP - 11 EP - 6 JF - Acta biochimica Polonica JO - Acta Biochim. Pol. VL - 59 IS - 1 N2 - Carotenoids and their metabolites are essential factors for the maintenance of important life processes such as photosynthesis. Animals cannot synthesize carotenoids de novo, they must obtain them via their food. In order to make intensive animal husbandry possible and maintain human and animal health synthetic nature identical carotenoids are presently commercially available at the multi-tonnes scale per year. Synthetically accessible (13)C enriched carotenoids are essential to apply isotope sensitive techniques to obtain information at the atomic level without perturbation about the role of carotenoids in photosynthesis, nutrition, vision, animal development, etc. Simple highly (13)C enriched C(1), C(2) and C(3) building blocks are commercially available via 99% (13)CO. The synthetic routes for the preparation of the (13)C enriched building blocks starting from the commercially available systems are discussed first. Then, how these building blocks are used for the synthesis of the various (13)C enriched carotenoids and apocarotenoids are reviewed next. The synthetic Schemes that resulted in (13)C enriched β-carotene, spheroidene, β-cryptoxanthin, canthaxanthin, astaxanthin, (3R,3'R)-zeaxanthin and (3R,3'R,6'R)-lutein are described. The Schemes that are reviewed can also be used to synthetically access any carotenoid and apocarotenoid in any (13)C isotopically enriched form up to the unitarily enriched form. SN - 1734-154X UR - https://www.unboundmedicine.com/medline/citation/22428113/Synthesis_of_highly_13C_enriched_carotenoids:_access_to_carotenoids_enriched_with_13C_at_any_position_and_combination_of_positions_ L2 - http://www.actabp.pl/pdf/1_2012/11.pdf DB - PRIME DP - Unbound Medicine ER -