Enantioselective Photochromism of Diarylethenes in Human Serum Albumin

Authors

  • Mai Fukagawa,

    1. Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501 (Japan), Fax: (+81)45-339-3934
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  • Dr. Izuru Kawamura,

    1. Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501 (Japan), Fax: (+81)45-339-3934
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  • Dr. Takashi Ubukata,

    1. Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501 (Japan), Fax: (+81)45-339-3934
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  • Prof. Yasushi Yokoyama

    Corresponding author
    1. Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501 (Japan), Fax: (+81)45-339-3934
    • Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501 (Japan), Fax: (+81)45-339-3934

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Abstract

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Making light work of chromism: Enantioselective photochromic ring-closing reactions of three bisthienylethene compounds possessing either no or two hydroxy groups were carried out in the hydrophobic pockets of human serum albumin (HSA) in aqueous media. When 10 equivalents of HSA were used, 1,2-bis(5-hydroxymethyl-2-methyl-3-thienyl)hexafluorocyclopentene predominantly produced the S,S closed form (see scheme; O=open, C=closed), in 63 % ee at RT and 71 % ee at −4 °C upon irradiation with 313 nm light.

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