A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′-benzothiazolyl)-thiazole-4-carboxylic acid] from 1,4-benzoquinone

被引：10

作者：

Ciuffreda, Pierangela ^{[1
]}

Casati, Silvana ^{[1
]}

Meroni, Giuseppe ^{[2
]}

Santaniello, Enzo ^{[2
]}

机构：

[1] Univ Milan, Dipartimento Sci Biomed & Clin L Sacco, I-20157 Milan, Italy

[2] Univ Milan, Dipartimento Sci Salute, I-20142 Milan, Italy

来源：

TETRAHEDRON | 2013年 / 69卷 / 29期

关键词：

Dehydroluciferin; Firefly luciferase; Natural products; Heterocycles; Total synthesis; LUCIFERASE GENE-EXPRESSION; FIREFLY LUCIFERASE; IN-VIVO; LIVING MICE; BIOLUMINESCENCE; PET; BENZOTHIAZOLES; DERIVATIVES; ANALOGS; SPECT;

D O I：

10.1016/j.tet.2013.05.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of dehydroluciferin [2-(6'-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid], the oxidative product of luciferin, has been realized starting from 1,4-benzoquinone. Reaction of this compound with L-cysteine ethyl ester, followed by an oxidation-cyclization step afforded 2-carbethoxy-6-hydroxybenzothiazole that was in situ hydrolyzed and decarboxylated to 6-hydroxybenzothiazole. The tert-butyl(dimethyl)silyl ether of this key intermediate was subjected to alpha-lithiation followed by formylation with DMF, and the resulting aldehyde condensed with L-cysteine ethyl ester. Dehydrogenation of the intermediate thiazolidine followed by deprotection afforded dehydroluciferin in 35% overall yield from 1,4-benzoquinone (69% from 6-hydroxybenzothiazole). (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5893 / 5897

页数：5

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