W.L. Noorduin, A.A.C. Bode, M. van
der Meijden, H. Meekes, A.F. van Etteger, W.J.P. van Enckevort, P.C. M.
Christianen, B. Kaptein, R.M. Kellogg, T. Rasing, E. Vlieg,
Complete
chiral symmetry breaking of an amino acid derivative directed by
circularly polarized light,
Nature Chemistry 1 (2009) 729-732
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.