Organophosphorus Analogues and Derivatives of the Natural l-Amino Carboxylic Acids and Peptides. III. Synthesis and Enzyme-Substrate Interactions of d-, Dl-, and l-5-Dihydroxyphosphinyl-3,4-didehydronorvaline and Their Cyclic Analogues and Derivatives
- 1 October 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 61 (10) , 3711-3715
- https://doi.org/10.1246/bcsj.61.3711
Abstract
The unusual natural amino acid phosphorus containing didehydronorvaline (5) has been synthesized by consecutive treatment of the 4-bromo-2-butenal (1) with potassium cyanide and ammonium carbonate to the hydantoin (2), converted into the organophosphorus derivative 3, followed by enzyme-catalyzed hydrolysis of the diethoxyphosphinyl group to the phosphonic acid 4, and hydrolysis. The tetrahydro-1,2-azaphosphorine (8) and the protected didehydronorvaline derivatives 6, 7, 9, and 10, have been synthesized.Keywords
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