The origin of homochirality of life. The first observation of MChD in organic compounds
Y. Kitagawa, H. Segawa, and K. Ishii
“Magneto-Chiral Dichroism of Organic Compounds”
Angew. Chem. Int. Ed., 50, 9133-9136 (2011).
(Very Important Paper, Cover Picture)
Homochirality of life, the biased distributions of L-amino acids and D-sugars, is still unsolved. Because Magneto-chiral dichroism (MChD) of two enantiomers is opposite in nature, MChD is one of plausible candidates for explaining the homochirality of life. However, MChD of organic compounds that constitute life has not yet been reported in contrast to several examples of MChD of metal compounds.
We succeeded in carrying out the first observation of MChD in organic compounds using chiral J-aggregates of water-soluble porphyrins. Because the MChD originates from the π-electronic properties of aggregates of conventional organic aromatic compounds, the MChD of the π-π* transitions not only has significant advantages such as tunable wavelengths and high chemical reactivity which are useful for asymmetric synthetic methods and magneto-optical devices, but also opens up new possibilities for clarifying the asymmetry in biological systems.
S. Hattori, S. Vandendriessche, G. Koeckelberghs, T. Verbiest and K.Ishii
"Evaporation rate-based selection of supramolecular chirality"
Chem. Commun., 53, 3066-3069 (2017).
S. Hattori, K. Akagawa, K. Kudo, and K. Ishii
"Determination of the Absolute Configuration of Side Chains of Basic Amino Acid Residues Using the Water-Soluble Porphyrin-Based Exciton Chirality Method"
J. Phys. Chem. B, 120, 10280-10287 (2016).
S. Hattori, Y. Yamamoto, T. Miyatake and K. Ishii
"Magneto-chiral dichroism measurements using a pulsed electromagnet"
Chem. Phys. Lett., 647, 38-41 (2017).
Y. Kitagawa, T. Miyatake, and K. Ishii
"Magneto-Chiral Dichroism of Artificial Light-Harvesting Antenna"
Chem. Commun., 48, 5091-5093 (2012).
Y. Kitagawa, J. Hiromoto, and K. Ishii
"Electronic Absorption, MCD, and Luminescence Properties of Porphyrin J-Aggregates"
J. Porphyrins Phthalocyanines, 17, 703-711 (2013).
S. Hattori, and K. Ishii
"Magneto-Chiral Dichroism of Aromatic π-Conjugated Systems"
Optical Material Express, 4, 11, 2423-2432 (2014).
Reported in the Media
- “Homochirality: A magnetic answer” NPG Asia Materials, Featured highlights, 03 October 2011.
- “Magenetochiral effect in Amphiphilic Porphyrin J-Aggregates” Angew. Chem. Int. Ed. Highlights, 50, 2-5 (2011).