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Convergence of Catalytic Antibody and Terpene Cyclase Mechanisms: Polyene Cyclization Directed by Carbocation–π Interactions
Author(s) -
Paschall Chiana M.,
Hasserodt Jens,
Jones Terri,
Lerner Richard A.,
Janda Kim D.,
Christianson David W.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990614)38:12<1743::aid-anie1743>3.0.co;2-3
Subject(s) - carbocation , polyene , chemistry , cyclase , catalysis , stereochemistry , hapten , cationic polymerization , combinatorial chemistry , organic chemistry , enzyme , antibody , biology , immunology
A tandem cationic cyclization cascade similar to a terpenoid cyclase reaction is catalyzed by antibody HA5‐19A4. The 2.7‐Å resolution crystal structure of the Fab–hapten complex reveals convergence with the same catalytic strategy employed by a terpenoid cyclase: both serve as templates that enforce the productive conformation of a flexible polyene substrate, and both stabilize carbocation intermediates through cation–π interactions with multiple aromatic residues in their active sites.