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Enamine/imine tautomerism in α,β-unsaturated-α-amino acids

✍ Scribed by S.-P. Lu; Anita H. Lewin

Book ID: 104208937
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 549 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00908-9

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✦ Synopsis

Investigation of the t~,l~-unsaturated-o~-amino acids--dehydrovaline, debydrophenylalanine, and debydropipecolinic acid---revealed that these compounds undergo rapid hydrolysis in neutral aqueous medium, via the imine tautomers, even when the corresponding esters and sodium salts exist as the enamine tautomers. This is true even for dehydropipecolinic acid which had been reported to be stable for I 0-18 b in dilute aqueous neutral solution.

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