The Reduction of Trifluoroacetophenone by Methyl-substituted Dihydronicotinamides

Bossaerts, J.; Dommisse, Roger; Alderweireldt, F. C.

doi:10.3987/r-1986-01-0115

HETEROCYCLES

1986

DOI: 10.3987/r-1986-01-0115

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The Reduction of Trifluoroacetophenone by Methyl-substituted Dihydronicotinamides

J. Bossaerts¹,

Roger Dommisse²,

F. C. Alderweireldt³

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1986

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Cited by 3 publications

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Quantifizierung der Reduktiven Aminierung in Nichtenzymatischer Aminosäuresynthese

Mayer

Moran

2022

Angewandte Chemie

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Die Biosynthese von Aminosäuren beginnt mit der reduktiven Aminierung von α‐Ketoglutarat mit Ammoniak, wobei Glutamat entsteht. Die anderen α‐Ketosäuren, die aus dem Glyoxylat‐ oder Krebszyklus stammen, werden jedoch eher durch Transaminierung als durch reduktive Aminierung in Aminosäuren umgewandelt. Warum wird nur eine Aminosäure durch reduktive Aminierung synthetisiert und die anderen nicht? Um diese Frage zu untersuchen, haben wir die intrinsischen Reaktivitäten von Ketosäuren in nichtenzymatischen Reduktionen und reduktiven Aminierungen unter Verwendung von BH3CN− als Modellnucleophil quantifiziert. Dabei wurde festgestellt, dass biologische α‐Ketosäuren ausgeprägte nichtenzymatische Reaktivitätsunterschiede für die Bildung von Aminosäuren aufweisen (α‐Ketoglutarat

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Quantifizierung der Reduktiven Aminierung in Nichtenzymatischer Aminosäuresynthese

Mayer

Moran

2022

Angewandte Chemie

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Quantifying Reductive Amination in Nonenzymatic Amino Acid Synthesis

Mayer

Moran

2022

Angew Chem Int Ed

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Amino acid biosynthesis initiates with the reductive amination of α-ketoglutarate with ammonia to produce glutamate. However, the other α-keto acids derived from the glyoxylate and Krebs cycles are converted into amino acids by transamination, rather than by reductive amination. Why is only one amino acid synthesized by reductive amination and not the others? To explore this question, we quantified the inherent reactivities of keto acids in nonenzymatic reduction and reductive amination by using BH 3 CN À as a model nucleophile. Biological α-keto acids were found to show pronounced nonenzymatic reactivity differences for the formation of amino acids (α-ketoglutarate < oxaloacetate � pyruvate ! glyoxylate). Accordingly, the flow of ammonia passes through the least reactive αketo acid of the Krebs cycle. One possible explanation for this choice is the position of the corresponding amino acid, glutamate, at the top of the thermodynamic landscape for subsequent transamination reactions.

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ChemInform Abstract: The Reduction of Trifluoroacetophenone by Methy1‐Substituted Dihydronicotinamides.

Bossaerts¹,

Dommisse²,

Alderweireldt³

1986

Chemischer Informationsdienst

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The Reduction of Trifluoroacetophenone by Methyl-substituted Dihydronicotinamides

Cited by 3 publications

References 0 publications

Quantifizierung der Reduktiven Aminierung in Nichtenzymatischer Aminosäuresynthese

Quantifizierung der Reduktiven Aminierung in Nichtenzymatischer Aminosäuresynthese

Quantifying Reductive Amination in Nonenzymatic Amino Acid Synthesis

ChemInform Abstract: The Reduction of Trifluoroacetophenone by Methy1‐Substituted Dihydronicotinamides.

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