Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin

Silke E. Bode; Daniel Drochner; Michael Müller

doi:10.1002/ange.200701014

journal article Jul 25, 2007

Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin

Silke E. Bode Daniel Drochner Michael Müller

Angewandte Chemie Vol. 119 No. 31 pp. 6020-6024 · Wiley

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References

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Originally racemic 7‐O‐desmethyl semivioxanthin (rac‐[10‐13C]4)13C labeled at C10 was synthesized by a similar route to semivioxanthin (2) synthesis. The13C label was introduced by13CO2addition to 2 6‐dimethoxy‐4‐methylbromobenzene. Feeding experiments withrac‐[10‐13C]4as the substrate revealed incorporation into metabolites1and2 but by13C NMR spectroscopy only one signal heightened for C10 C10′ was observed in the putatively diastereomeric vioxanthin products. Thus no conclusion regarding the detection of the three diastereomers was possible. Therefore a 1:1 mixture of (R)‐[1‐13C]4(8 mg) and (S)‐[1‐13C]4(8 mg) was used for a feeding experiment with racemic [1‐13C]4.

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All other13C NMR signals were not distinguishable for the two diastereomers. A mixture of synthesized (P R R)‐1 (P S S)‐1 and (P R/S R/S)‐1showed similar13C NMR spectra with two carbonyl signals atδ=171.61 ppm andδ=171.57 ppm.

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Although the correctP R R configuration for natural vioxanthin (1) fromP. citreoviridehas been proposed by Zeeck et al. (reference [7]) their approach to confirm this is not valid: The CD spectra of1in the range of 300–450 nm is not predominantly determined by the chirality of the stereogenic centers but rather by the axial chirality.

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Details

Published: Jul 25, 2007
Vol/Issue: 119(31)
Pages: 6020-6024
License: View

Authors

Nutrition, Metabolism and Genomics Group, Wageningen University, Wageningen, the Netherlands; Netherlands Nutrigenomics Centre, Top Institute Food and Nutrition, Wageningen, the Netherlands

Cite This Article

Silke E. Bode, Daniel Drochner, Michael Müller (2007). Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin. Angewandte Chemie, 119(31), 6020-6024. https://doi.org/10.1002/ange.200701014

Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin

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