Synthesis of l-Kynurenine and Homo-l-Kynurenine via an Aza-Fries Rearrangement

Edgar Bonilla-Reyes; Adrian Sánchez-Carrillo; Alfredo Vázquez

doi:10.1055/s-0040-1707223

Synthesis, Table of Contents

Synthesis 2020; 52(22): 3473-3479
DOI: 10.1055/s-0040-1707223

paper

Synthesis of l-Kynurenine and Homo-l-Kynurenine via an Aza-Fries Rearrangement

Edgar Bonilla-Reyes

^aDepartamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Cd. Mx., México Email: joseavm@unam.mx

,

Adrian Sánchez-Carrillo

^bLaboratorio de Investigación en Inmunoquímica, Hospital Infantil de México Federico Gómez, Dr. Márquez 162, Col Doctores, Cuauhtémoc, 06720, Cd. Mx., México

,

Alfredo Vázquez∗

^aDepartamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Cd. Mx., México Email: joseavm@unam.mx

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Abstract

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Abstract

l-Kynurenine, a non-proteinogenic amino acid, is the primary metabolite of tryptophan via the kynurenine pathway. Kynurenine is involved in a variety of biological processes occurring in the human body, notably in the central nervous system. Thus, the study of this molecule offers multiple opportunities for drug discovery; however, an essential prelude for biological studies is to secure the supply of kynurenine and analogues thereof. A simple synthetic procedure for the efficient preparation of enantiomerically pure l-kynurenine from l-aspartic acid and its implementation to prepare homo-l-kynurenine from l-glutamic acid is presented. The approach relies on a photochemical aza-Fries rearrangement of the corresponding acyl-aniline as the fundamental transformation.

Key words

l-kynurenine - homo-l-kynurenine - non-proteinogenic amino acids - aza-Fries - photochemical rearrangement

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References

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