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

doi:10.1055/S-0029-1217971

Paper

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

Published Oct 1, 2009 · G. Meroni, P. Ciana, A. Maggi

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Abstract

2-Cyano-6-hydroxybenzothiazole is the key intermediate for the synthesis of D-luciferin, the natural substrate of firefly luciferases. A new synthesis of2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with L-cysteine ethyl ester, followed by 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 nearly quantitative yield (90-95%).

Study Snapshot

This study presents a new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate for the synthesis of D-luciferin, using 1,4-benzoquinone and L-cysteine ethyl ester.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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