12626-73-2Relevant academic research and scientific papers
Biosynthesis of indigo in Escherichia coli expressing self-sufficient CYP102A from Streptomyces cattleya
Kim, Hee-Jung,Jang, Seyoung,Kim, Joonwon,Yang, Yung-Hun,Kim, Yun-Gon,Kim, Byung-Gee,Choi, Kwon-Young
, p. 29 - 35 (2017)
Cytochrome P450 monooxygenases (CYP) are a superfamily of heme-thiolate proteins which catalyze the incorporation of oxygen atoms into substrates. Here, a self-sufficient CYP102A from Streptomyces cattleya (CYP102A_scat) was cloned, produced recombinantly in Escherichia coli strain BL21 (DE3), and the characteristic features were investigated. However, unlike other self-sufficient CYP102A enzymes that have been reported, CYP102A_scat was found to be able to catalyze intracellular hydroxylation of indole molecules with 3-C specific regioselectivity. Consequently, E.?coli strains producing CYP102A_scat could synthesize approximately 1.0?g/L of indigo in LB media. Optimization of indigo synthesis was investigated through additional feeding of indole precursors such as glucose, L-tryptophan, and indole. Indigo production reached up to 3.8?±?0.1?g/L by adding 20?μM of extracellular indole and 0.2?mM of L-tryptophan to the LB media. To our knowledge, this is a record and the highest yield achieved so far.
Solving the clogging problem: Precipitate-forming reactions in flow
Poe, Sarah L.,Cummings, Meredith A.,Haaf, Michael P.,McQuade, D. Tyler
, p. 1544 - 1548 (2006)
Solids go with the flow: A monodisperse flow in a microreactor provides an efficient method for keeping solid products away from channel walls. The use of a carrier phase, such as mineral oil, hexane, or toluene, enables solids to be synthesized without clogging of the reactor channels. Further injection points can be added to the microreactor to perform multistep syntheses (see picture). (Figure Presented)
Determination of acetylcholinesterase and butyrylcholinesterase activity without dilution of biological samples
Pohanka, Miroslav
, p. 1044 - 1049 (2015)
Two cholinesterases: acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), are known. The enzymes are important in the body and alteration of their activity has significant use in the diagnosis of poisoning, liver function, etc. Currently available methods for the determination of cholinesterases have some major drawbacks including various interferences and the inability to be used for decreasing the enzyme activity in the presence of reversible inhibitors due to sample dilution; hence, a method for dilution free assay of cholinesterases is desired. Here, microplates were modified with indoxylacetate (100 μL of 10 mmol L-1 solution) and used for cholinesterases assay after drying at 37 °C. The fact that indoxylacetate remains stable in dry state and serves simultaneously as a chromogen and substrate provide good prerequisites for the method. The limit of detection for BChE was 0.71 U while that for AChE was 2.8 U per a 100 μL sample (solution of enzyme or plasma sample). The limit of detection is low enough to allow standard examination of cholinesterasemia. The two cholinesterases can be distinguished from each other using selective inhibitors such as donepezil and iso-OMPA. The new method was also successfully validated for the standard Ellman's assay using plasma samples with BChE activity adjusted by carbofuran. The new method based on indoxylacetate seems promising for routine tests.
Green and efficient biosynthesis of indigo from indole by engineered myoglobins
Liu, Can,Xu, Jiakun,Gao, Shu-Qin,He, Bo,Wei, Chuan-Wan,Wang, Xiao-Juan,Wang, Zhonghua,Lin, Ying-Wu
, p. 33325 - 33330 (2018)
With the demand nowadays for blue dyes, it is of practical importance to develop a green and efficient biocatalyst for the production of indigo. The design of artificial enzymes has been shown to be attractive in recent years. In a previous study, we engineered a single mutant of sperm whale myoglobin, F43Y Mb, with a novel Tyr-heme cross-link. In this study, we found that it can efficiently catalyze the oxidation of indole to indigo, with a yield as high as 54% compared to the highest yield (～20%) reported to date in the literature. By further modifying the heme active site, we engineered a double mutant of F43Y/H64D Mb, which exhibited the highest catalytic efficiency (198 M?1 s?1) among the artificial enzymes designed in Mb. Moreover, both F43Y Mb and F43Y/H64D Mb were found to produce the indigo product with a chemoselectivity as high as ～80%. Based on the reaction system, we also established a convenient and green dyeing method by dyeing a cotton textile during the biosynthesis of indigo, followed by further spraying the concentrated indigo, without the need of strong acids/bases or any reducing agents. The successful application of dyeing a white cotton textile with a blue color further indicates that the designed enzyme and the dyeing method have practical applications in the future.
A cyclodextrin-based molecular reactor to template the formation of indigoid dyes
Harper, Jason B.,Easton, Christopher J.,Lincoln, Stephen F.
, p. 5815 - 5818 (2003)
N,N′-Bis(6A-deoxy-β-cyclodextrin-6 A-yl)urea behaves as a molecular reactor to bias competing reactions of indoxyl anion and isatin-5-sulfonate in water, to give indigo and indirubin-5′-sulfonate. It appears that the cyclodextrin dimer increases the relative reactivity of the isatin-5-sulfonate, by selectively complexing the reactive form. The molecular host also aligns the isatinsulfonate with indoxyl anion to favour production of indirubin-5′-sulfonate, with the result that the ratio of indigo and indirubin-5′-sulfonate produced is altered by a factor of at least 3500, without a substantial loss of yield.
Effects of Organic Solvents on Indigo Formation by Pseudomonas sp. strain ST-200 Grown with High Levels of Indole
Doukyu, Noriyuki,Arai, Tomonori,Aono, Rikizo
, p. 1075 - 1080 (1998)
The indole tolerance level of Pseudomonas sp. strain ST-200 was 0.25 mg/ml. The level was raised to 4 mg/ml when diphenylmethane was added to the medium to 20% by volume. ST-200 grown in this two-phase culture system containing indole (1 mg/ml) and diphenylmethane (0.2 ml/ml) produced a water-soluble yellow pigment, isatic acid, and two water-insoluble and diphenylmethane-soluble pigments, blue indigo and purple indirubin. The amounts of the water-insoluble pigments corresponded to 0.5% (indigo) and 0.2% (indirubin) of the indole added to the medium. Of the conditions tried, indigo and indirubin were formed only when ST-200 was grown in the two-phase system overlaid with organic solvents with appropriate polarity.
Bromo-substituted cibalackrot backbone, a versatile donor or acceptor main core for organic optoelectronic devices
Din?alp, Haluk,Saltan, G?zde Murat,Zafer, Ceylan,K?ymaz, Deniz Aykut
, p. 512 - 520 (2018)
Cibalackrot (Ci-I), one of the latest highly conjugated compound possessing bis-lactam structure, was investigated with respect to their brominated derivatives in order to determine their suitable substitution points for the syntheses of new class of small molecules for optoelectronic devices. 7,14-Bis(4-bromophenyl) (Ci-II) and 3,10-dibromo (Ci-III) derivatives of cibalackrot possess moderately narrow band gaps of 2.15 and 2.09 eV, respectively. Notably, Ci-III dye exhibits more red-shifted ultraviolet–visible (UV–vis) absorption and fluorescence emission spectra as compared to that of Ci-II dye because Ci-III shows more prominent intramolecular charge transfer (ICT) complex than that of Ci-II dye. Electron mobilities of the order of 7.0 × 10?4 cm2/V and 3.1 × 10?4 cm2/V were measured using Ci-II and Ci-III as active layer, respectively. Charge transfer properties of the molecules were investigated in bulk heterojunction device configuration wherein Ci-III showed p-type behavior against n-type PCBM in photovoltaic device. Photovoltaic performance of Ci-III dye which was used as donor component is 20 times higher than that of the device in which this dye was used as acceptor.
NMR spectroscopic study of the Murex trunculus dyeing process
Hoffman, Rina C.,Zilber, Reut C.,Hoffman, Roy E.
, p. 892 - 895 (2010)
It is widely accepted that indigo dyes derived from Murex trunculus were used to produce the biblical dyes tekhelet and argaman. We describe a method of following the debromination of natural leucoindigos and their binding to wool using NMR spectroscopy. Debromination is observed prior to reaction with the wool and prior to oxidation. Binding to the wool is shown to occur prior to oxidation. NMR allows the dyeing process to be followed. This, in principle, could be used to correct problems during dyeing that would increase the reliability of the process. Copyright
Identification of broad specificity P450CAM variants by primary screening against indole as substrate
Celik, Ayhan,Speight, Robert E.,Turner, Nicholas J.
, p. 3652 - 3654 (2005)
High-throughput screening of cytochrome P450CAM libraries, for their ability to oxidise indole to indigo and indirubin, has resulted in the identification of variants with activity towards the structurally unrelated substrate diphenylmethane. The Royal Society of Chemistry 2005.
Novel reactivity of dibenzothiophene monooxygenase from bacillus subtilis WU-S2B
Ohshiro, Takashi,Nakura, Shuhei,Ishii, Yoshitaka,Kino, Kuniki,Kirimura, Kohtaro,Izumi, Yoshikazu
, p. 2128 - 2130 (2009)
Dibenzothiophene monooxygenase (BdsC) from Bacillus subtilis WU-S2B utilized aromatic compounds not having sulfur atoms as substrates. It acted on indole and its derivatives to form indigoid pigments, and also utilized indoline and phenoxazine. In additio
