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Enantioselective photochromism of diarylethenes in human serum albumin.

Fukagawa M, Kawamura I, Ubukata T, Yokoyama Y.

Chemistry. 2013 Jul 15;19(29):9434-7.

Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501, Japan.




Photochromism is defined as the reversible transformation of a chemical species induced by light irradiation. Diarylethenes are one of the most promising photochromic compounds exhibiting photochemical ring closure and ring opening via 6-electrocyclization since they are highly fatigue resistive. We have long been interested in stereoselective photochromic reactions, and have recently focused on the chirality transfer to the photochromic molecules from their surrounding environments through the photoreactions. This paper deals with the enantioselective photochromic ring-closing reactions of bisthienyl ethenes possessing no or two hydroxygroups in the hydrophobic and chiral pockets of human serum albumin (HSA) in aqueous media. When 10 equivalents of HSA was used, 1,2-bis(5-hydroxymethyl-2-methyl-3-thienyl)hexafluorocyclopentene predominantly produced the (S,S)-closed form with 63% ee at r.t. and 71% eeat -4 oC upon 313-nm light irradiation. The frontispiece on the cover page of this issue illustrates the content of this paper.

The X-ray image of HSA in the figure was provided courtesy of the RCSB PDB (Code 4K2C with Simple Viewer 4.1.0).

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DOI: 10.1002/chem.201301459




Cover Picture: DOI: 10.1002/chem.201390105.



Enantioselective Photochromism of Diarylethenes in Human Serum Albumin