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Design and Synthesis of Haptens for the Catalytic Antibody‐Promoted Dynamic Kinetic Resolution of Oxazolin‐5‐ones
Author(s) -
Briot Anne,
Bujard Murielle,
Gouverneur Véronique,
Mioskowski Charles
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(20021)2002:1<139::aid-ejoc139>3.0.co;2-s
Subject(s) - hapten , chemistry , phosphinate , kinetic resolution , hydrolysis , combinatorial chemistry , catalysis , derivative (finance) , organic chemistry , enantioselective synthesis , antibody , fire retardant , economics , financial economics , immunology , biology
The synthesis of the first two haptens designed to elicit catalytic hydrolytic antibodies for the dynamic kinetic resolution of racemic 4‐substituted 4 H ‐oxazolin‐5‐ones is reported. A cyclic phosphinate and a 2,5‐dihydro‐1 H ‐pyrrolium derivative were chosen as “first generation” haptens. The cyclic phosphinate was designed to mimic the higher energy transition state along the reaction coordinate for the hydrolytic process, while the dihydro‐1 H ‐pyrrolium group of the second hapten was selected to generate hydrolytic antibodies that might use a “bait and switch” mechanism. These two haptens were prepared successfully by use of a ring‐closing metathesis reaction as the key step. This study is the first pilot investigation towards an antibody‐promoted dynamic kinetic resolution and should allow the development of a new biocatalytic route to enantiomerically pure natural and unnatural amino acids.