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Photocontrol of the Catalytic Activity of a β ‐Cyclodextrin Bearing Azobenzene and Histidine Moieties as a Pendant Group
Author(s) -
Lee WooSang,
Ueno Akihiko
Publication year - 2001
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/1521-3927(20010301)22:6<448::aid-marc448>3.0.co;2-w
Subject(s) - azobenzene , moiety , cyclodextrin , chemistry , imidazole , catalysis , hydrolysis , histidine , polymer chemistry , azo compound , stereochemistry , organic chemistry , enzyme , molecule , polymer
Abstract An azobenzene group was linked to β ‐cyclodextrin via a histidine spacer ( 1 ) to produce a photoresponsive catalyst. The ester hydrolysis of p ‐nitrophenyl acetate, Boc‐ L ‐alanine‐ p ‐nitrophenyl ester and Boc‐ D ‐alanine‐ p ‐nitrophenyl ester was examined in the presence of trans ‐ 1 or cis ‐ 1 . In the case of cis ‐ 1 , the cyclodextrin cavity was used as the substrate binding site during imidazole‐catalyzed ester hydrolysis. This was not possible in the case of trans ‐ 1 due to the inclusion of the trans ‐azobenzene moiety in the cyclodextrin cavity. Consequently, the catalytic mechanism switches in an on‐off fashion on UV irradiation, associated with the conversion of the azobenzene moiety of 1 from trans to cis .