Making Glycine Methyl Ester Chiral

• Published in: Chemistry : a European journal 2018-08, Vol.24 (46), p.11904-11907
• Main Authors: Gerbig, Dennis, Desch, Sarina, Schreiner, Peter R.
• Format: Article
• Language: English
• Subjects: Amino acids; Chemistry; Chirality; chirality transfer; chirogenesis; Circular dichroism; Comets; Dichroism; Glycine; Lactic acid; matrix isolation; Optical activity; Spectroscopy; vibrational circular dichroism; vibrational optical activity
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201802119

We demonstrate that the simple achiral amino acid glycine as its methyl ester inherits the chiral imprint of methyl lactate upon complexation, resulting in induced vibrational optical activity of the methylene C−H bonds. To mimic conditions of ice on comets that are considered long‐term reaction as well as storage entities for (organic) molecules, we employ the matrix isolation technique in conjunction with vibrational circular dichroism spectroscopy and DFT computations. The observed chirality transfer is likely a key element for the realization of concepts rationalizing chirogenesis, that is, the generation of a chiral imbalance. Komm gib mir deine Händigkeit: Chirality transfer from methyl lactate to the methyl ester of achiral amino acid glycine has been observed by means of matrix isolation vibrational circular dichroism spectroscopy: Under model conditions similar to those in cometary ices, glycine methyl ester, upon complexation, obtains distinct vibrational optical activity. More generally, chirality transfer could be a key to selective activation of enantiomeric molecular complexes, resulting in enantiomeric enrichment. Background of the Image is credited to: ESA—European Space Agency, ESA/Rosetta/NAVCAM–CC BY‐SA 3.0 IGO. Background image is an adaptation from: www.flickr.com/photos/europeanspaceagency/15984172995/ and is distributed with the same CC BY‐SA 3.0 IGO license.