Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-10-08 , DOI: 10.1016/j.dyepig.2018.10.009 Seyun Namgung , Hyun A. Park , Joonwon Kim , Pyung-Gang Lee , Byung-Gee Kim , Yung-Hun Yang , Kwon-Young Choi
In this study, the biosynthesis of various indigoids with novel spectral features and antibacterial activities was investigated. First, 12 indole derivatives as substrates were biotransformed into functional indigoid dyes by E. coli cells expressing CYP102G4 hydroxylase. The indole derivatives included chloro (Cl-), nitro (NO2-), hydroxy (HO-), methoxy (CH3O-), methyl (CH3-), carboxy (COOH-), amino (NH3-), and cyano (CN-) indoles at the C4 to C7 positions. Interestingly, dramatic color shifts were observed from blue to red, green, purple, and even pink depending on the functional groups and their positions. Next, the biological and physical properties, antibacterial effects, and dying fastness of the prepared compounds were investigated and visually measured. Among the synthesized indigoid dyes, 6,6’-dichloroindigo and 5,5’-dichloroindigo showed the relatively higher cell growth inhibitory activity in the liquid phase. Finally, a one-pot producing strain which produced 7,7’-dichloroindigo from l-tryptophan using tryptophan-7-halogenase (PrnA) and CYP102G4 simultaneously was developed to overcome the disadvantages of uneconomical semi-synthesis through indole precursor feedstocks. The developed producing strain produced approximately 15.4 ± 1.4 mg/L of 7,7’-dichloroindigo in 24 h. To the best of our knowledge, this is the first report of the production of 7,7’-dichloroindigo in E. coli via a one-pot process.
中文翻译:
使用CYP102G4和PrnA卤化酶进行一锅式靛蓝衍生物染料的生态友好型生物合成
在这项研究中,研究了具有新颖光谱特征和抗菌活性的各种靛类的生物合成。首先,通过表达CYP102G4羟化酶的大肠杆菌将12种吲哚衍生物作为底物生物转化为功能性靛蓝染料。吲哚衍生物包括氯(Cl-),硝基(NO 2-),羟基(HO-),甲氧基(CH 3 O-),甲基(CH 3-),羧基(COOH-),氨基(NH 3-)和C4至C7位置的氰基(CN-)吲哚。有趣的是,根据官能团及其位置,观察到了从蓝色到红色,绿色,紫色甚至粉红的剧烈色移。接下来,对制备的化合物的生物学和物理性质,抗菌作用和染色牢度进行了研究并目测。在合成的靛类染料中,6,6'-二氯靛蓝和5,5'-二氯靛蓝在液相中显示出相对较高的细胞生长抑制活性。最后,产生一锅的菌株,该菌株从l产生了7,7'-dichloroindigo同时开发了使用色氨酸7-卤化酶(PrnA)和CYP102G4的β-色氨酸,以克服通过吲哚前体原料进行不经济的半合成的缺点。发达的生产菌株在24小时内产生了约15.4±1.4 mg / L的7,7'-二氯靛蓝。据我们所知,这是首次通过一锅法在大肠杆菌中生产7,7'-dichloroindigo的报告。