TY - JOUR
T1 - Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis
AU - Matsumoto, Arimasa
AU - Ozaki, Hanae
AU - Tsuchiya, Sumeru
AU - Asahi, Toru
AU - Lahav, Meir
AU - Kawasaki, Tsuneomi
AU - Soai, Kenso
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science and MEXT-Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016.
Publisher Copyright:
© The Royal Society of Chemistry 2019.
PY - 2019
Y1 - 2019
N2 - Chiral crystals of the only achiral proteinogenic α-amino acid, glycine induced the asymmetric autocatalysis with amplification of enantiomeric excess (ee). The P31 crystals of γ-glycine, which display positive Cotton effect (CD) at around 215 nm, mediate the asymmetric autocatalysis to yield (R)-pyrimidyl alkanol with high ee. In contrast, the enantiomorphic P32 crystals, which display negative Cotton effect, afford (S)-alkanol after the significant amplification of ee by asymmetric autocatalysis.
AB - Chiral crystals of the only achiral proteinogenic α-amino acid, glycine induced the asymmetric autocatalysis with amplification of enantiomeric excess (ee). The P31 crystals of γ-glycine, which display positive Cotton effect (CD) at around 215 nm, mediate the asymmetric autocatalysis to yield (R)-pyrimidyl alkanol with high ee. In contrast, the enantiomorphic P32 crystals, which display negative Cotton effect, afford (S)-alkanol after the significant amplification of ee by asymmetric autocatalysis.
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U2 - 10.1039/c9ob00345b
DO - 10.1039/c9ob00345b
M3 - Article
C2 - 30932119
AN - SCOPUS:85065150968
VL - 17
SP - 4200
EP - 4203
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 17
ER -