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Making Glycine Methyl Ester Chiral
Author(s) -
Gerbig Dennis,
Desch Sarina,
Schreiner Peter R.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802119
Subject(s) - chirality (physics) , glycine , circular dichroism , chemistry , vibrational circular dichroism , molecule , methylene , matrix isolation , realization (probability) , stereochemistry , matrix (chemical analysis) , computational chemistry , spectroscopy , amino acid , organic chemistry , chiral symmetry , physics , biochemistry , statistics , mathematics , chromatography , quantum mechanics , nambu–jona lasinio model , quark
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.