172479-59-3Relevant academic research and scientific papers
Synthesis of l -Kynurenine and Homo- l -Kynurenine via an Aza-Fries Rearrangement
Bonilla-Reyes, Edgar,Sánchez-Carrillo, Adrian,Vázquez, Alfredo
, p. 3473 - 3479 (2020/09/15)
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 st
Carbonylative coupling of organozinc reagents in the presence and absence of aryl iodides: Synthesis of unsymmetrical and symmetrical ketones
Jackson, Richard F. W.,Turner, Debra,Block, Michael H.
, p. 865 - 870 (2007/10/03)
The utility of the palladium(o) catalysed reaction of the iodoalanine-derived organozinc reagent 6a with functionalised aryl iodides, under a carbon monoxide atmosphere, to give protected 4-aryl-4-oxo α-amino acids 8, is illustrated by a short synthesis of L-kynurenine 4. Treatment of functionalised organozinc reagents with catalytic tetrakis(triphenylphosphine)palladium(0) under an atmosphere of carbon monoxide in the absence of any electrophile leads to the formation of symmetrical functionalised ketones 9 in good yields. This reaction is illustrated by a one-step synthesis of protected (2S,6S)-4-oxo-2,6-diaminopimelic acid 9a from commercially available compounds. It has been established that adventitious molecular oxygen plays a key role in the formation of the symmetrical ketones 9, and that rigorous exclusion of oxygen can result in substantially higher yields of ketones 8 in the cross-coupling with some aromatic iodides.
Carbonylative coupling of an amino acid-derived organozine reagent with functionalized aryl iodides: Synthesis of kynurenine
Jackson,Turner,Block
, p. 2207 - 2208 (2007/10/02)
The utility of the palladium(o) catalysed reaction of the serine-derived organozinc reagent 6 with functionalized aryl iodides, under a carbon monoxide atmosphere, to give protected 4-aryl-4-oxo α-amino acids 8 is illustrated by a short synthesis of L-kynurenine.
