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Title: Employing a biochemical protecting group for a sustainable indigo dyeing strategy

Abstract

All rights reserved. Indigo is an ancient dye uniquely capable of producing the signature tones in blue denim; however, the dyeing process requires chemical steps that are environmentally damaging. Here, we describe a sustainable dyeing strategy that not only circumvents the use of toxic reagents for indigo chemical synthesis but also removes the need for a reducing agent for dye solubilization. This strategy utilizes a glucose moiety as a biochemical protecting group to stabilize the reactive indigo precursor indoxyl to form indican, preventing spontaneous oxidation to crystalline indigo during microbial fermentation. Application of a β-glucosidase removes the protecting group from indican, resulting in indigo crystal formation in the cotton fibers. We identified the gene coding for the glucosyltransferase PtUGT1 from the indigo plant Polygonum tinctorium and solved the structure of PtUGT1. Heterologous expression of PtUGT1 in Escherichia coli supported high indican conversion, and biosynthesized indican was used to dye cotton swatches and a garment.

Authors:
ORCiD logo [1];  [2]; ORCiD logo [3];  [4];  [4];  [5]; ORCiD logo [6]
  1. Univ. of California, Berkeley, CA (United States). Dept. of Bioengineering, and UC Berkeley-UCSF Graduate Program in Bioengineering
  2. Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Biophysics and Integrated Bioimaging Division; Technical Univ. of Denmark, Lyngby (Denmark). Novo Nordisk Foundation Center for Biosustainability
  3. Univ. of California, Berkeley, CA (United States). Dept. of Bioengineering, and UC Berkeley-UCSF Graduate Program in Bioengineering; Technical Univ. of Denmark, Lyngby (Denmark). Novo Nordisk Foundation Center for Biosustainability
  4. Univ. of California, Berkeley, CA (United States). Dept. of Bioengineering; Technical Univ. of Denmark, Lyngby (Denmark). Novo Nordisk Foundation Center for Biosustainability
  5. Univ. of California, Berkeley, CA (United States). Dept. of Bioengineering; Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Biophysics and Integrated Bioimaging Division
  6. Univ. of California, Berkeley, CA (United States). Dept. of Bioengineering; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Biological Systems & Engineering Division
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1485082
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Nature Chemical Biology
Additional Journal Information:
Journal Volume: 14; Journal Issue: 3; Journal ID: ISSN 1552-4450
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Hsu, Tammy M., Welner, Ditte H., Russ, Zachary N., Cervantes, Bernardo, Prathuri, Ramya L., Adams, Paul D., and Dueber, John E.. Employing a biochemical protecting group for a sustainable indigo dyeing strategy. United States: N. p., 2018. Web. doi:10.1038/nchembio.2552.
Hsu, Tammy M., Welner, Ditte H., Russ, Zachary N., Cervantes, Bernardo, Prathuri, Ramya L., Adams, Paul D., & Dueber, John E.. Employing a biochemical protecting group for a sustainable indigo dyeing strategy. United States. doi:10.1038/nchembio.2552.
Hsu, Tammy M., Welner, Ditte H., Russ, Zachary N., Cervantes, Bernardo, Prathuri, Ramya L., Adams, Paul D., and Dueber, John E.. Mon . "Employing a biochemical protecting group for a sustainable indigo dyeing strategy". United States. doi:10.1038/nchembio.2552. https://www.osti.gov/servlets/purl/1485082.
@article{osti_1485082,
title = {Employing a biochemical protecting group for a sustainable indigo dyeing strategy},
author = {Hsu, Tammy M. and Welner, Ditte H. and Russ, Zachary N. and Cervantes, Bernardo and Prathuri, Ramya L. and Adams, Paul D. and Dueber, John E.},
abstractNote = {All rights reserved. Indigo is an ancient dye uniquely capable of producing the signature tones in blue denim; however, the dyeing process requires chemical steps that are environmentally damaging. Here, we describe a sustainable dyeing strategy that not only circumvents the use of toxic reagents for indigo chemical synthesis but also removes the need for a reducing agent for dye solubilization. This strategy utilizes a glucose moiety as a biochemical protecting group to stabilize the reactive indigo precursor indoxyl to form indican, preventing spontaneous oxidation to crystalline indigo during microbial fermentation. Application of a β-glucosidase removes the protecting group from indican, resulting in indigo crystal formation in the cotton fibers. We identified the gene coding for the glucosyltransferase PtUGT1 from the indigo plant Polygonum tinctorium and solved the structure of PtUGT1. Heterologous expression of PtUGT1 in Escherichia coli supported high indican conversion, and biosynthesized indican was used to dye cotton swatches and a garment.},
doi = {10.1038/nchembio.2552},
journal = {Nature Chemical Biology},
number = 3,
volume = 14,
place = {United States},
year = {Mon Jan 08 00:00:00 EST 2018},
month = {Mon Jan 08 00:00:00 EST 2018}
}

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Cited by: 6 works
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