AMINO ANALOGS OF FIREFLY LUCIFERIN AND BIOLOGICAL ACTIVITY THEREOF
AMINO ANALOGS OF FIREFLY LUCIFERIN AND BIOLOGICAL ACTIVITY THEREOF
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DOI：
10.1021/ja00961a030
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发表时间：
1966-01-01
影响因子：
15
通讯作者：
MCELROY, WD
中科院分区：
文献类型：
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作者：
WHITE, EH;WORTHER, H;MCELROY, WD
为了研究萤火虫的生物发光机理，我们使用了化合物2-（6′-氨基-2′-苯并噻唑）- a2 -噻唑！合成了ine-4-羧酸（IVa，“氨基荧光素”）、2-（6′-乙酰氨基-2′-苯并噻唑基）- a2 -噻唑-4-羧酸（IVb）和2-（6′-三氟乙酰氨基-2′-苯并噻唑基）- a2 -噻唑-4-羧酸（IVc）。在这些化合物中，只有氨基荧光素与萤火虫荧光素酶和ATP反应产生光。与天然荧光素的反应不同，天然荧光素在中性和碱性pH下发出黄绿色荧光，在酸性pH下发出红色荧光。将氨基荧光素的荧光与天然荧光素的荧光进行比较。
For our study of the mechanism of firefly bioluminescence, the compounds 2-(6'-amino-2'-benzothiazolyl)-A2-thiazo! ine-4-carboxylic acid (IVa,“aminoluciferin”), 2-(6'-acetylamino-2'-benzothiazolyl)-A2-thiazoline-4-carboxylic acid (IVb), and 2-(6'-trifluoroacetylamino-2'-benzothiazolyl)-A2-thiazoline-4-carboxylic acid (IVc) have been synthesized and characterized. Of these compounds, only aminoluciferin reacts with firefly luciferase and ATP to produce light. The bioluminescence emission is red and is pH independent, unlike the reactionwith natural luciferin, which emits in the yellow-green at neutral and alkaline pH and in the red at acid pH. The fluo-rescence of aminoluciferin is compared with that of native luciferin.