Reaction of 3-nitrotyrosine with HOCl in aq. phosphate buffer (pH 7.4) leads to a mixt. of extractable products, including 3,5-bis(4-hydroxy-3-nitrophenyl)pyridine (15% isolated yield) and 3,5-bis(4-hydroxy-3-nitrophenyl)-2-[(4-hydroxy-3-nitrophenyl)methyl]pyridine (3%) arising by a Chichibabin-like pyridine synthesis via N-chloro imine intermediates. Under the same conditions, phenylalanine gives 3,5-diphenylpyridine in 9% isolated yield, while tyrosine leads to 3,5-bis(4-hydroxyphenyl)pyridine (3%) and 3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)pyridine (3%).
Remarkable Chichibabin-type cyclotrimerisation of 3-nitrotyrosine, tyrosine and phenylalanine to 3,5-diphenylpyridine derivatives induced by hypochlorous acid / Panzella, Lucia; P., DI DONATO; S., Comes; Napolitano, Alessandra; A., Palumbo; D'Ischia, Marco. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 46:38(2005), pp. 6457-6460. [10.1016/j.tetlet.2005.07.106]
Remarkable Chichibabin-type cyclotrimerisation of 3-nitrotyrosine, tyrosine and phenylalanine to 3,5-diphenylpyridine derivatives induced by hypochlorous acid.
PANZELLA, LUCIA;NAPOLITANO, ALESSANDRA;D'ISCHIA, MARCO
2005
Abstract
Reaction of 3-nitrotyrosine with HOCl in aq. phosphate buffer (pH 7.4) leads to a mixt. of extractable products, including 3,5-bis(4-hydroxy-3-nitrophenyl)pyridine (15% isolated yield) and 3,5-bis(4-hydroxy-3-nitrophenyl)-2-[(4-hydroxy-3-nitrophenyl)methyl]pyridine (3%) arising by a Chichibabin-like pyridine synthesis via N-chloro imine intermediates. Under the same conditions, phenylalanine gives 3,5-diphenylpyridine in 9% isolated yield, while tyrosine leads to 3,5-bis(4-hydroxyphenyl)pyridine (3%) and 3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)pyridine (3%).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
