Ecofriendly one-pot biosynthesis of indigo derivative dyes using CYP102G4 and PrnA halogenase

Namgung, Seyun; Park, Hyun A.; Kim, Joonwon; Lee, Pyung‐Gang; Kim, Byung‐Gee; Yang, Yung‐Hun; Choi, Kwon‐Young

doi:10.1016/j.dyepig.2018.10.009

Cited by 49 publications

(25 citation statements)

References 40 publications

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“…Natural indigo (C.I. 75780), mazarine powder extracted from the indigo plant, is one of the earliest and most popular vat dyestuffs [1,2]. Recently, the demand for natural indigo dye is increasing dramatically for its safety and biodegradability.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Sun²,

Liu

2019

Molecules

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This paper presents a comparative study on natural indigo and indirubin in terms of molecular structures and spectral properties by using both computational and experimental methods. The spectral properties were analyzed with Fourier transform infrared (FTIR), Raman, UV-Visible, and fluorescence techniques. The density functional theory (DFT) method with B3LYP using 6-311G(d,p) basis set was utilized to obtain their optimized geometric structures and calculate the molecular electrostatic potential, frontier molecular orbitals, FTIR, and Raman spectra. The single-excitation configuration interaction (CIS), time-dependent density functional theory (TD-DFT), and polarization continuum model (PCM) were used to optimize the excited state structure and calculate the UV-Visible absorption and fluorescence spectra of the two molecules at B3LYP/6-311G(d,p) level. The results showed that all computational spectra agreed well with the experimental results. It was found that the same vibrational mode presents a lower frequency in indigo than that in indirubin. The frontier molecular orbital analysis demonstrated that the UV-Visible absorption and fluorescence bands of indigo and indirubin are mainly derived from π → π* transition. The results also implied that the indigo molecule is more conjugated and planar than indirubin, thereby exhibiting a longer maximum absorption wavelength and stronger fluorescence peak.

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Section: Introductionmentioning

confidence: 99%

Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Sun²,

Liu

2019

Molecules

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“…S. glaucescens melanin was applied for cotton dyeing and use as functional fibers. The manufacture of functional cotton materials dyed with melanin was conducted based on the results of the evaluation of the cotton fiber dyeing performance of previously reported indigo-based dyes [ 20 ]. A 10 cm × 10 cm cotton sheet was prepared and stained with the melanin culture supernatant first.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, an attempt to design and engineer the physiological functionalities of melanin by introducing new radical precursors into melanin synthetic pathways has been reported. For example, 3-hydroxyindole was introduced by expressing a cytochrome P450 monooxygenase (CYP) enzyme that mediates a site-specific hydroxylation reaction to indole C3 position in eumelanin biosynthesis, and the generated novel melanin showed different physical functionalities [ 20 ]. Also, electrochemical properties of synthetic melanin have been reported to widen the sphere of its application to the field of electrochemistry [ 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Microbial Production of Melanin Pigments from Caffeic Acid and L-Tyrosine Using Streptomyces glaucescens and FCS-ECH-Expressing Escherichia coli

Ahn

Jang

Sudheer

et al. 2021

IJMS

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In this study, synthetic allomelanin was prepared from wild-type Streptomyces glaucescens and recombinant Escherichia coli BL21(DE3) strains. S. glaucescens could produce 125.25 ± 6.01 mg/L of melanin with a supply of 5 mM caffeic acid within 144 h. The ABTS radical scavenging capacity of S. glaucescens melanin was determined to be approximately 7.89 mg/mL of IC50 value, which was comparable to L-tyrosine-based eumelanin. The isolated melanin was used in cotton fabric dyeing, and the effect of copper ions, laccase enzyme treatment, and the dyeing cycle on dyeing performance was investigated. Interestingly, dyeing fastness was greatly improved upon treatment with the laccase enzyme during the cotton dyeing process. Besides, the supply of C5-diamine, which was reported to lead to more complex crosslinking between melanin units, to caffeic acid-based melanin synthesis was also investigated for higher production and novel functionalities. To facilitate the supply of caffeic acid and C5-diamine, E. coli strains expressing each or combinations of tyrosine ammonia lyase/p-coumarate 3-hydroxylase, feruloyl-CoA synthetase/enoyl-CoA hydratase/aldolase, and tyrosinase/lysine decarboxylase enzymes were prepared and investigated for their eumelanin, C5-diamine, and allomelanin production from L-tyrosine and L-lysine, respectively. Finally, H-NMR, FT-IR, and MALDI-TOF analysis of the synthetic melanin pigments were attempted to obtain the chemical information.

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“…The well‐known indoxyl (3‐hydroxyindole) can be synthesized by introducing a hydroxyl moiety through a monooxygenase enzyme reaction at the indole C3 position 52. Subsequent oxidation of indoxyl leads to the generation of indoxyl radicals, and two molecules of indoxyl radicals are converted to a well‐known blue‐colored indigo dye‐a symmetric dimer‐through a self‐dimerization reaction 53–57. According to recent studies, several monooxygenases such as flavin monooxygenase (FMO), cytochrome P450 monooxygenase (CYP), toluene dioxygenase (TDO), and naphthalene dioxygenase (NDO) were involved in indole C3‐hydroxylation and bio‐indigo formation from L‐tryptophan 58–64.…”

Section: Deamination Of Aromatic Amino Acids and Cosmetic And Pharmaceutical Applicationsmentioning

confidence: 99%

Nitrogen‐Neutral Amino Acids Refinery: Deamination of Amino Acids for Bio‐Alcohol and Ammonia Production

Choi

2021

ChemBioEng Reviews

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Amino acids are a valuable bioresource that contains both the acid form of carbon and the amine group of nitrogen. Amino acids not only constitute proteins and the building blocks for living organisms but also provide a key intermediate for controlling the nitrogen balance in cells. The production of amino acids using microorganisms has, along with the development of biotechnology, created a large market for biochemicals. In parallel, there have been various biochemical production methods using pulmonary proteins or direct amino acids as biomass through enzymatic bioconversion or whole‐cell biotransformation. The deamination of amino acids facilitated the applications of 2‐keto and acrylic acids, in particular, for biofuels of bio alcohol, pharmaceuticals, cosmetics, as building blocks for polymers, and other versatile industrial chemicals. In this review, we report on the application of amino acids derived from biochemicals initiated by deamination reactions using deaminase, ammonia‐lyase, and oxidase enzymes for biotechnology applications.

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Ecofriendly one-pot biosynthesis of indigo derivative dyes using CYP102G4 and PrnA halogenase

Cited by 49 publications

References 40 publications

Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Molecular Structures and Spectral Properties of Natural Indigo and Indirubin: Experimental and DFT Studies

Microbial Production of Melanin Pigments from Caffeic Acid and L-Tyrosine Using Streptomyces glaucescens and FCS-ECH-Expressing Escherichia coli

Nitrogen‐Neutral Amino Acids Refinery: Deamination of Amino Acids for Bio‐Alcohol and Ammonia Production

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