A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1,4-benzoquinone
Articolo
Data di Pubblicazione:
2009
Citazione:
A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1,4-benzoquinone / G. Meroni, P. Ciana, A.C. Maggi, E. Santaniello. - In: SYNLETT. - ISSN 0936-5214. - 2009:16(2009), pp. 2682-2684. [10.1055/s-0029-1217971]
Abstract:
2-cyano-6-hydroxybenzothiazole is the key intermediate for the synthesis of D-luciferin, the natural substrate of firefly luciferases. A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with L-cysteine ethyl ester, followed by an oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propanoate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and a conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone). This nitrile reacts with D-cysteine to afford D-luciferin at room temperature in a nearly quantitative yield (90-95%).
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
1,4-benzoquinone; 2-cyano- 6-hydroxybenzothiazole; D-luciferin; Firefly luciferase
Elenco autori:
G. Meroni, P. Ciana, A.C. Maggi, E. Santaniello
Link alla scheda completa: