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An Antibody‐Catalyzed 1,2‐Rearrangement of CarbonCarbon Bonds
Author(s) -
Chen Yuanwei,
Reymond JeanLouis,
Lerner Richard A.
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199416071
Subject(s) - hapten , catalysis , chemistry , cope rearrangement , carbon fibers , phenol , transition (genetics) , photochemistry , stereochemistry , antibody , organic chemistry , materials science , biology , biochemistry , immunology , composite number , composite material , gene
The transition state of the dienone‐phenol rearrangement of 1 to 2 is mimicked by hapten 3 . An immune response to 3 yielded an antibody (62C7) which was found to catalyze the rearrangement efficiently. It was shown that 62C7 does not act as a simple acid catalyst, but rather selectively stabilizes the charge distribution in the transition state.