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Enantioselective Photochromism of Diarylethenes in Human Serum Albumin
Author(s) -
Fukagawa Mai,
Kawamura Izuru,
Ubukata Takashi,
Yokoyama Yasushi
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301459
Subject(s) - photochromism , hydroxymethyl , human serum albumin , enantioselective synthesis , bovine serum albumin , chemistry , computer science , aqueous medium , aqueous solution , stereochemistry , organic chemistry , chromatography , catalysis
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.