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Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli
by
Lee, Jeongchan
, Kim, Joonwon
, Kim, Yun-Gon
, Song, Ji Eun
, Jeong, Hee-Jin
, Kim, Byung-Gee
, Choi, Kwon-Young
, Kim, Hye Rim
, Song, Won-Suk
, Kim, Eun-Jung
in
631/553/318
/ 631/92/60
/ 631/92/607
/ Biochemical Engineering
/ Biochemistry
/ Biocompatibility
/ Biocompatible Materials - chemistry
/ Biocompatible Materials - metabolism
/ Biodegradation
/ Bioorganic Chemistry
/ Bromination
/ Cell Biology
/ Chemistry
/ Chemistry and Materials Science
/ Chemistry/Food Science
/ Cloning, Molecular
/ Coloring Agents - isolation & purification
/ Coloring Agents - metabolism
/ Dimethylaniline monooxygenase (N-oxide-forming)
/ Dyes
/ E coli
/ Escherichia coli
/ Escherichia coli - enzymology
/ Escherichia coli - genetics
/ Escherichia coli Proteins - genetics
/ Escherichia coli Proteins - metabolism
/ Flavin
/ Flavin reductase
/ Flavin-Adenine Dinucleotide - analogs & derivatives
/ Flavin-Adenine Dinucleotide - metabolism
/ FMN Reductase - genetics
/ FMN Reductase - metabolism
/ Gene Expression
/ Gene Expression Regulation, Bacterial
/ Genetic Vectors - chemistry
/ Genetic Vectors - metabolism
/ Halogenation
/ Indigo Carmine - isolation & purification
/ Indigo Carmine - metabolism
/ Indoles - isolation & purification
/ Indoles - metabolism
/ Metabolic Engineering - methods
/ Oxidoreductases - genetics
/ Oxidoreductases - metabolism
/ Oxygenases - genetics
/ Oxygenases - metabolism
/ Recombinant Proteins - genetics
/ Recombinant Proteins - metabolism
/ Reductases
/ Semiconductor materials
/ Semiconductors
/ Snails
/ Stereoisomerism
/ Synthesis
/ Tryptophan
/ Tryptophan - metabolism
/ Tryptophan 2,3-dioxygenase
/ Tryptophanase - genetics
/ Tryptophanase - metabolism
2021
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Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli
by
Lee, Jeongchan
, Kim, Joonwon
, Kim, Yun-Gon
, Song, Ji Eun
, Jeong, Hee-Jin
, Kim, Byung-Gee
, Choi, Kwon-Young
, Kim, Hye Rim
, Song, Won-Suk
, Kim, Eun-Jung
in
631/553/318
/ 631/92/60
/ 631/92/607
/ Biochemical Engineering
/ Biochemistry
/ Biocompatibility
/ Biocompatible Materials - chemistry
/ Biocompatible Materials - metabolism
/ Biodegradation
/ Bioorganic Chemistry
/ Bromination
/ Cell Biology
/ Chemistry
/ Chemistry and Materials Science
/ Chemistry/Food Science
/ Cloning, Molecular
/ Coloring Agents - isolation & purification
/ Coloring Agents - metabolism
/ Dimethylaniline monooxygenase (N-oxide-forming)
/ Dyes
/ E coli
/ Escherichia coli
/ Escherichia coli - enzymology
/ Escherichia coli - genetics
/ Escherichia coli Proteins - genetics
/ Escherichia coli Proteins - metabolism
/ Flavin
/ Flavin reductase
/ Flavin-Adenine Dinucleotide - analogs & derivatives
/ Flavin-Adenine Dinucleotide - metabolism
/ FMN Reductase - genetics
/ FMN Reductase - metabolism
/ Gene Expression
/ Gene Expression Regulation, Bacterial
/ Genetic Vectors - chemistry
/ Genetic Vectors - metabolism
/ Halogenation
/ Indigo Carmine - isolation & purification
/ Indigo Carmine - metabolism
/ Indoles - isolation & purification
/ Indoles - metabolism
/ Metabolic Engineering - methods
/ Oxidoreductases - genetics
/ Oxidoreductases - metabolism
/ Oxygenases - genetics
/ Oxygenases - metabolism
/ Recombinant Proteins - genetics
/ Recombinant Proteins - metabolism
/ Reductases
/ Semiconductor materials
/ Semiconductors
/ Snails
/ Stereoisomerism
/ Synthesis
/ Tryptophan
/ Tryptophan - metabolism
/ Tryptophan 2,3-dioxygenase
/ Tryptophanase - genetics
/ Tryptophanase - metabolism
2021
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Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli
by
Lee, Jeongchan
, Kim, Joonwon
, Kim, Yun-Gon
, Song, Ji Eun
, Jeong, Hee-Jin
, Kim, Byung-Gee
, Choi, Kwon-Young
, Kim, Hye Rim
, Song, Won-Suk
, Kim, Eun-Jung
in
631/553/318
/ 631/92/60
/ 631/92/607
/ Biochemical Engineering
/ Biochemistry
/ Biocompatibility
/ Biocompatible Materials - chemistry
/ Biocompatible Materials - metabolism
/ Biodegradation
/ Bioorganic Chemistry
/ Bromination
/ Cell Biology
/ Chemistry
/ Chemistry and Materials Science
/ Chemistry/Food Science
/ Cloning, Molecular
/ Coloring Agents - isolation & purification
/ Coloring Agents - metabolism
/ Dimethylaniline monooxygenase (N-oxide-forming)
/ Dyes
/ E coli
/ Escherichia coli
/ Escherichia coli - enzymology
/ Escherichia coli - genetics
/ Escherichia coli Proteins - genetics
/ Escherichia coli Proteins - metabolism
/ Flavin
/ Flavin reductase
/ Flavin-Adenine Dinucleotide - analogs & derivatives
/ Flavin-Adenine Dinucleotide - metabolism
/ FMN Reductase - genetics
/ FMN Reductase - metabolism
/ Gene Expression
/ Gene Expression Regulation, Bacterial
/ Genetic Vectors - chemistry
/ Genetic Vectors - metabolism
/ Halogenation
/ Indigo Carmine - isolation & purification
/ Indigo Carmine - metabolism
/ Indoles - isolation & purification
/ Indoles - metabolism
/ Metabolic Engineering - methods
/ Oxidoreductases - genetics
/ Oxidoreductases - metabolism
/ Oxygenases - genetics
/ Oxygenases - metabolism
/ Recombinant Proteins - genetics
/ Recombinant Proteins - metabolism
/ Reductases
/ Semiconductor materials
/ Semiconductors
/ Snails
/ Stereoisomerism
/ Synthesis
/ Tryptophan
/ Tryptophan - metabolism
/ Tryptophan 2,3-dioxygenase
/ Tryptophanase - genetics
/ Tryptophanase - metabolism
2021
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Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli
Journal Article
Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli
2021
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Overview
Tyrian purple, mainly composed of 6,6'-dibromoindigo (6BrIG), is an ancient dye extracted from sea snails and was recently demonstrated as a biocompatible semiconductor material. However, its synthesis remains limited due to uncharacterized biosynthetic pathways and the difficulty of regiospecific bromination. Here, we introduce an effective 6BrIG production strategy in
Escherichia coli
using tryptophan 6-halogenase SttH, tryptophanase TnaA and flavin-containing monooxygenase MaFMO. Since tryptophan halogenases are expressed in highly insoluble forms in
E. coli
, a flavin reductase (Fre) that regenerates FADH
2
for the halogenase reaction was used as an N-terminal soluble tag of SttH. A consecutive two-cell reaction system was designed to overproduce regiospecifically brominated precursors of 6BrIG by spatiotemporal separation of bromination and bromotryptophan degradation. These approaches led to 315.0 mg l
−1
6BrIG production from tryptophan and successful synthesis of regiospecifically dihalogenated indigos. Furthermore, it was demonstrated that 6BrIG overproducing cells can be directly used as a bacterial dye.
A two-cell setup containing tryptophanase, a flavin-dependent monooxygenase and a regiospecific halogenase (linked to a flavin reductase as a solubility tag) enables the production of 6,6'-dibromoindigo and other indigoid dyes in
Escherichia coli
.
Publisher
Nature Publishing Group US,Nature Publishing Group
Subject
/ Biocompatible Materials - chemistry
/ Biocompatible Materials - metabolism
/ Chemistry and Materials Science
/ Coloring Agents - isolation & purification
/ Coloring Agents - metabolism
/ Dimethylaniline monooxygenase (N-oxide-forming)
/ Dyes
/ E coli
/ Escherichia coli - enzymology
/ Escherichia coli Proteins - genetics
/ Escherichia coli Proteins - metabolism
/ Flavin
/ Flavin-Adenine Dinucleotide - analogs & derivatives
/ Flavin-Adenine Dinucleotide - metabolism
/ Gene Expression Regulation, Bacterial
/ Genetic Vectors - metabolism
/ Indigo Carmine - isolation & purification
/ Indoles - isolation & purification
/ Metabolic Engineering - methods
/ Oxidoreductases - metabolism
/ Recombinant Proteins - genetics
/ Recombinant Proteins - metabolism
/ Snails
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