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Reference type: Journal
Authors: Arora PS, Van QN, Famulok M, Shaka AJ, Nowick JS
Article Title: Design and synthesis of a transition state analogue for the Diels-Alder reaction.
Publication date: 1998
Journal: Bioorganic & Medicinal Chemistry
Volume: 6
Issue: (9)
Page numbers: 1421-1428.
DOI: 10.1016/S0968-0896(98)00072-8

Abstract: This paper describes the design and synthesis of a tricationic transition state analogue (TSA 1) for the Diels-Alder reaction. TSA 1 contains a bicyclo[2.2.1]heptene ring system that mimics the boat conformation of the Diels-Alder transition state and is designed to bind tightly to antibodies, nucleic acids, and imprinted polymers by means of hydrogen bonds and salt-bridges. This paper also describes the syntheses of the Diels-Alder reaction substrates (diene 2 and dienophile 3) and a sensitive HPLC assay to monitor the formation of Diels-Alder product 4. In contrast to previously reported TSAs and dienophiles for the Diels-Alder reaction that are based upon maleimides, TSA 1 and dienophile 3 are based upon fumaramide. The fumaramide system should destabilize the initially formed boat conformer of Diels-Alder product 4 and stabilize a half-chair conformer. The conversion of the initially formed boat conformer to the half-chair conformer is designed to help prevent Diels-Alder product 4 from binding strongly to catalysts selected to strongly bind TSA 1. This feature should minimize product inhibition, which can be a problem in the catalysis of the Diels-Alder reaction. (C) 1998 Elsevier Science Ltd. All rights reserved


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