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Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light

Nature Chemistry volume 1, pages 729–732 (2009)Cite this article

Abstract

Circularly polarized light (CPL) emitted from star-forming regions is an attractive candidate as a cause of single chirality in nature. It has remained difficult, however, to translate the relatively small chemical effects observed on irradiation of molecular systems with CPL into high enantiomeric excesses. Here we demonstrate that irradiation of a racemic amino acid derivative with CPL leads to a small amount of chiral induction that can be amplified readily to give an enantiopure solid phase. A racemate composed of equal amounts of left- and right-handed crystals in contact with the irradiated solution is converted completely into crystals of single-handedness through abrasive grinding when racemization is effected in the solution. The rotation sense of the CPL fully determines the handedness of the final solid state. These findings illustrate the potential effectiveness of CPL in the control of molecular asymmetry, which is relevant for the origin of the single chirality inherent to many biological molecules.

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Figure 1: Experimental set-up for CPL-driven deracemization.
Figure 2: Solution racemization kinetics, CPL absorption spectra and solid-phase deracemization of 1 from an initial enantioimbalance.
Figure 3: Cascade of events during the CPL-directed deracemization of racemic 1.

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Acknowledgements

The SNN agency (Cooperation Northern Netherlands) and the European Fund for Regional Development (EFRO) are acknowledged for partial financial support of this work. A.J. Toonen is acknowledged for technical assistance. W.L.N acknowledges A.J. Noorduin for stimulating discussions. W.L.N. and E.V. thank COST Action CM0703 for support.

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Authors and Affiliations

  1. Radboud University Nijmegen, Solid State Chemistry, Heyendaalseweg 135, Nijmegen, 6525, AJ, Netherlands

    Wim L. Noorduin, Arno A. C. Bode, Hugo Meekes, Albert F. van Etteger, Willem J. P. van Enckevort, Peter C. M. Christianen, Theo Rasing & Elias Vlieg

  2. Syncom BV, Kadijk 3, Groningen, 9747, AT, Netherlands

    Maarten van der Meijden & Richard M. Kellogg

  3. DSM Pharmaceutical Products, Innovative Synthesis & Catalysis, Geleen, Netherlands

    Bernard Kaptein

Authors
  1. Wim L. Noorduin
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  11. Elias Vlieg
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Contributions

W.L.N conceived, designed and performed experiments and co-wrote the paper. A.A.C.B. co-designed and performed experiments. M.M. synthesized and analysed compounds and performed nonpolarized light experiments. H.M. co-designed experiments, discussed the results and co-wrote the paper. A.F.E. designed the experimental CPL setup and provided technical assistance. W.J.P.E. and P.C.M.C. discussed the results and commented on the manuscript. B.K., R.M.K., T.R. and E.V. supervised the research and co-wrote the paper.

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Correspondence to Elias Vlieg.

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Noorduin, W., Bode, A., van der Meijden, M. et al. Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light. Nature Chem 1, 729–732 (2009). https://doi.org/10.1038/nchem.416

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