D-Cysteine → 2-(6-Hydroxybenzo[d]thiazol-2-yl)-2,5-dihydrothiazole-4-carboxylic acid

HRID 2045754Notes

Reaction equation

HRID 2045754 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[C:13]([C:15]1[S:16][C:17]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:18]=2[N:19]=1)#[N:14].N[C@@H:26]([C:29]([OH:31])=[O:30])[CH2:27][SH:28]>>[OH:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([CH:1]3[N:2]=[C:26]([C:29]([OH:31])=[O:30])[CH2:27][S:28]3)[S:4][C:5]=2[CH:11]=1.[NH2:24][C:22]1[CH:21]=[CH:20][C:18]2[N:19]=[C:15]([CH:13]3[N:14]=[C:26]([C:29]([OH:31])=[O:30])[CH2:27][S:28]3)[S:16][C:17]=2[CH:23]=1

Participants

5

Reactant 3

HCID 92851D-CysteineHCID 98819122-Cyano-6-hydroxybenzothiazoleHCID 141571126-Amino-2-cyanobenzothiazole

Product 2

HCID 590468412-(6-Hydroxybenzo[d]thiazol-2-yl)-2,5-dihydrothiazole-4-carboxylic acidHCID 674179322-(6-Aminobenzo[d]thiazol-2-yl)-2,5-dihydrothiazole-4-carboxylic acid

Procedure

While 2-cyano-6-hydroxybenzothiazole or 2-cyano-6-aminobenzothiazole do not react with luciferase to generate light, both compounds readily cyclize with D-cysteine to form 2-(6-hydroxybenzo[d]thiazol-2-yl)-2,5-dihydrothiazole-4-carboxylic acid (D-luciferin) or 2-(6-aminobenzo[d]thiazol-2-yl)-2,5-dihydrothiazole-4-carboxylic acid (aminoluciferin), respectively, which do generate light when reacted with luciferase, e.g., at thermostable firefly luciferase. The assays can be performed at a pH of 4-9 with 1-100 μM derivative. Numerous non-luciferase enzymes may be detected and/or their activity measured in a bioluminescent assay using these derivatives.

Sources & evidence

ORD record
ord-ac747a0cb2af4f9db4b41221b6f3914e
Source dataset
uspto-grants-2013_11
Patent number
US08592172B2

Reaction notes

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