期刊
TETRAHEDRON
卷 57, 期 52, 页码 10299-10307出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)01048-1
关键词
antibodies; phosphinic acids and derivatives; palladium; coupling reactions
We describe herein the synthesis of a new unsymmetrical diarylphosphinic acid, a hapten aimed to produce catalytic antibodies for the hydrolysis of heterocyclic amides. The phosphinate functionality was selected as a mimic both of the tetrahedral intermediate and the transition state of higher energy along the reaction profile. The phenyl and 2,4,6-(trimethyl)-phenyl groups flanking the phosphinate were chosen in order to impose rotation around the P-C bond, a choice supported by ab initio calculations. This new hapten should elicit catalytic antibodies whose binding site could affect the distortion at nitrogen as well as the twist along the N-C(O) bond for heterocyclic amides. This hapten along with a series of new sterically hindered unsymmetrical phosphinic acid derivatives was prepared by a key palladium-catalysed step. (C) 2001 Elsevier Science Ltd. All rights reserved.
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