Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light.
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.
Radboud University Nijmegen, Solid State Chemistry, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
Wim L
WL
Noorduin
Arno A C
AA
Bode
Maarten
M
van der Meijden
Hugo
H
Meekes
Albert F
AF
van Etteger
Willem J P
WJ
van Enckevort
Peter C M
PC
Christianen
Bernard
B
Kaptein
Richard M
RM
Kellogg
Theo
T
Rasing
Elias
E
Vlieg
D000596:Amino Acids / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D008027:Light; D012996:Solutions / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013997:Time Factors
D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D012996:Solutions; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene