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%).

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.

A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1,4-benzoquinone

G. Meroni
Primo
;
P. Ciana
Secondo
;
A.C. Maggi
Penultimo
;
E. Santaniello
Ultimo
2009

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%).
1,4-benzoquinone; 2-cyano- 6-hydroxybenzothiazole; D-luciferin; Firefly luciferase
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/147469
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