Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule

Nature ◽  
1995 ◽  
Vol 378 (6559) ◽  
pp. 767-768 ◽  
Author(s):  
Kenso Soai ◽  
Takanori Shibata ◽  
Hiroshi Morioka ◽  
Kaori Choji
Keyword(s):  
Enantiomeric Excess ◽  
Chiral Molecule ◽  
Asymmetric Autocatalysis

scholarly journals Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess

2015 ◽  
Vol 54 (50) ◽  
pp. 15218-15221 ◽  
Author(s):  
Arimasa Matsumoto ◽  
Takaaki Abe ◽  
Atsushi Hara ◽  
Takayuki Tobita ◽  
Taisuke Sasagawa ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

2000 ◽  
Vol 11 (21) ◽  
pp. 4249-4253 ◽  
Author(s):  
Shigehisa Tanji ◽  
Yasutaka Kodaka ◽  
Atsushi Ohno ◽  
Takanori Shibata ◽  
Itaru Sato ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Self-Replication and Amplification of Enantiomeric Excess of Chiral Multifunctionalized Large Molecules by Asymmetric Autocatalysis

2014 ◽  
Vol 53 (42) ◽  
pp. 11199-11202 ◽  
Author(s):  
Tsuneomi Kawasaki ◽  
Mai Nakaoda ◽  
Yutaro Takahashi ◽  
Yusuke Kanto ◽  
Nanako Kuruhara ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Large Molecules ◽  
Asymmetric Autocatalysis ◽  
Self Replication

scholarly journals Asymmetric autocatalysis triggered by triglycine sulfate with switchable chirality by the direction of electric field

2021 ◽  
Author(s):  
Tsuneomi Kawasaki ◽  
Yoshiyasu Kaimori ◽  
Seiya Shimada ◽  
Natsuki Hara ◽  
Susumu Sato ◽  
...  
Keyword(s):  
Electric Field ◽  
Organic Compounds ◽  
Enantiomeric Excess ◽  
Triglycine Sulfate ◽  
Molecular Chirality ◽  
Asymmetric Autocatalysis ◽  
Soai Reaction

Triglycine sulfate (TGS) acts as a chiral trigger for asymmetric autocatalysis with amplification of enantiomeric excess, i.e., the Soai reaction. Therefore, molecular chirality of highly enantioenriched organic compounds is controlled...

ChemInform Abstract: Asymmetric Autocatalysis of 5-Carbamoyl-3-pyridyl Alkanols with Amplification of Enantiomeric Excess.

ChemInform ◽  
2001 ◽  
Vol 32 (14) ◽  
pp. no-no
Author(s):  
Shigehisa Tanji ◽  
Yasutaka Kodaka ◽  
Atsushi Ohno ◽  
Takanori Shibata ◽  
Itaru Sato ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Relationship between the time, yield, and enantiomeric excess of asymmetric autocatalysis of chiral 2-alkynyl-5-pyrimidyl alkanol with amplification of enantiomeric excess

2003 ◽  
Vol 14 (8) ◽  
pp. 975-979 ◽  
Author(s):  
Itaru Sato ◽  
Daisuke Omiya ◽  
Hiroyoshi Igarashi ◽  
Keiichi Kato ◽  
Yoshihiro Ogi ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Absolute Asymmetric Synthesis: A Commentary

2003 ◽  
Vol 68 (5) ◽  
pp. 849-864 ◽  
Author(s):  
Kurt Mislow
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomeric Excess ◽  
Optically Active ◽  
Random Chance ◽  
Chemical Reagents ◽  
Absolute Asymmetric Synthesis ◽  
Asymmetric Autocatalysis ◽  
Physical Forces ◽  
Biomolecular Homochirality ◽  
The Difference

Absolute asymmetric synthesis, i.e., the formation of enantiomerically enriched products from achiral precursors without the intervention of chiral chemical reagents or catalysts, is in practice unavoidable on statistical grounds alone. That random chance, combined with suitable amplification mechanisms, might ultimately account for biomolecular homochirality in Nature was recognized more than a century ago. Soai and collaborators have recently developed an asymmetric autocatalysis reaction that is capable of amplifying a tiny enantiomeric excess of far below 1% to yield a nearly enantiopure product. Although there is no easy way to tell the difference between an asymmetric autocatalysis reaction initiated by the tiny enantiomeric excess due to random chance and one initiated by minuscule quantities of unidentified chiral impurities, it is nevertheless all but certain that the Soai reaction is capable of producing optically active compounds by an absolute asymmetric synthesis, starting from nominally achiral reagents free of chiral contaminants and run under achiral conditions, e.g., without the intervention of chiral physical forces.

scholarly journals Amplification of enantiomeric excess by dynamic inversion of enantiomers in deracemization of Au38 clusters

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Yanan Wang ◽  
Belén Nieto-Ortega ◽  
Thomas Bürgi
Keyword(s):  
Symmetry Breaking ◽  
Ligand Exchange ◽  
Metal Clusters ◽  
Enantiomeric Excess ◽  
Dynamic Inversion ◽  
Chiral Molecule ◽  
Ligand Shell ◽  
Inorganic Matter ◽  
Left And Right ◽  
Cluster 2

Abstract Symmetry breaking and amplification processes have likely played a fundamental role in the development of homochirality on earth. Such processes have not been much studied for inorganic matter at the nanoscale. Here, we show that the balance between left- and right-handed intrinsically chiral metal clusters can be broken by adsorbing a small amount of a chiral molecule in its ligand shell. We studied the amplification of enantiomeric excess of the Au38(2-PET)24 cluster (2-PET = 2-phenylethylthiolate). By exchanging a small fraction of the achiral 2-PET ligand by chiral R-1,1′-binaphthyl-2,2′-dithiol (R-BINAS), a mixture of species is obtained composed of anticlockwise (A) and clockwise (C) versions of Au38(2-PET)24 and Au38(2-PET)22(R-BINAS)1. At 70 °C, the system evolves towards the anticlockwise clusters at the expense of the clockwise antipode. It is shown that the interplay between the diastereospecific ligand exchange, which introduces selectivity but does not change the A/C ratio, and the fast racemization of the Au38(2-PET)24 is at the origin of this observation.

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