Title: Fluoroimines from the reaction of fluoroamino acids or fluoroketo acids with the aldehyde or amine form of vitamin B6: Part III. Influence of fluorine on the formation and the reactivity of fluoroimines derived from β-fluoroaspartates or β-fluorooxaloacetate
Abstract: The introduction of fluorine at the β-position in aspartate and in oxaloacetate, the typical amino acid-keto acid couple in transamination, induces large effects in their reaction with respectively pyridoxal 5′-phosphate (PLP) (1) and pyridoxamine 5′-phosphate (PMP) (4). The formation of imine intermediates through reaction of 1 with erythro or threo-β-fluoroaspartate (2e and 2t) and through reaction of 4 with β-fluorooxaloacetate 5 is highly favored in comparison with that of non-fluoro compounds. The stereoisomers of the imines are unambiguously determined using a reduction reaction. The evolution of these intermediates shows that no transaminatlon is observed and that a dehydrofluorination occurs suggesting that the β-fluoro moiety in the intermediate turns into a good leaving group, changing the model reaction of transamination on α carbon through the aldimine-ketimine tautomerization to an elimination on β carbon.
Publication Year: 1985
Publication Date: 1985-04-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 2
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