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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},
issn = {1552-4450},
number = 3,
volume = 14,
place = {United States},
year = {2018},
month = {1}
}

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Cited by: 22 works
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Figures / Tables:

Figure 1 Figure 1: A glucosyl protecting group enables control over the timing and location of indigo dyeing

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L.</span> </li> <li> Proceedings of the National Academy of Sciences, Vol. 97, Issue 12, p. 6640-6645</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1073/pnas.120163297" class="text-muted" target="_blank" rel="noopener noreferrer">10.1073/pnas.120163297<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1016/j.phytochem.2008.12.009" target="_blank" rel="noopener noreferrer" class="name">Substrate specificity of plant UDP-dependent glycosyltransferases predicted from crystal structures and homology modeling<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2009-02-01">February 2009</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Osmani, Sarah A.; Bak, Søren; Møller, Birger Lindberg</span> </li> <li> Phytochemistry, Vol. 70, Issue 3</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1016/j.phytochem.2008.12.009" class="text-muted" target="_blank" rel="noopener noreferrer">10.1016/j.phytochem.2008.12.009<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1016/j.febslet.2009.09.042" target="_blank" rel="noopener noreferrer" class="name">Structure, mechanism and engineering of plant natural product glycosyltransferases<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2009-09-29">September 2009</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Wang, Xiaoqiang</span> </li> <li> FEBS Letters, Vol. 583, Issue 20</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1016/j.febslet.2009.09.042" class="text-muted" target="_blank" rel="noopener noreferrer">10.1016/j.febslet.2009.09.042<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1093/nar/gkv315" target="_blank" rel="noopener noreferrer" class="name">PLIP: fully automated protein–ligand interaction profiler<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2015-04-14">April 2015</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Salentin, Sebastian; Schreiber, Sven; Haupt, V. Joachim</span> </li> <li> Nucleic Acids Research, Vol. 43, Issue W1</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1093/nar/gkv315" class="text-muted" target="_blank" rel="noopener noreferrer">10.1093/nar/gkv315<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1126/sciadv.1501623" target="_blank" rel="noopener noreferrer" class="name">Early pre-Hispanic use of indigo blue in Peru<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2016-09-01">September 2016</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Splitstoser, Jeffrey C.; Dillehay, Tom D.; Wouters, Jan</span> </li> <li> Science Advances, Vol. 2, Issue 9</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1126/sciadv.1501623" class="text-muted" target="_blank" rel="noopener noreferrer">10.1126/sciadv.1501623<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1038/nchembio.1717" target="_blank" rel="noopener noreferrer" class="name">Acetylation serves as a protective group in noscapine biosynthesis in opium poppy<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2014-12-08">December 2014</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Dang, Thu-Thuy T.; Chen, Xue; Facchini, Peter J.</span> </li> <li> Nature Chemical Biology, Vol. 11, Issue 2</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1038/nchembio.1717" class="text-muted" target="_blank" rel="noopener noreferrer">10.1038/nchembio.1717<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1128/AEM.01448-15" target="_blank" rel="noopener noreferrer" class="name">Development of a Recombinant Escherichia coli Strain for Overproduction of the Plant Pigment Anthocyanin<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2015-07-06">July 2015</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Lim, Chin Giaw; Wong, Lynn; Bhan, Namita</span> </li> <li> Applied and Environmental Microbiology, Vol. 81, Issue 18</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1128/AEM.01448-15" class="text-muted" target="_blank" rel="noopener noreferrer">10.1128/AEM.01448-15<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1099/00207713-49-3-1025" target="_blank" rel="noopener noreferrer" class="name">An indigo-reducing moderate thermophile from a woad vat, Clostridium isatidis sp. nov.<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="1999-07-01">July 1999</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Padden, A. N.; Dillon, V. M.; Edmonds, J.</span> </li> <li> International Journal of Systematic Bacteriology, Vol. 49, Issue 3</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1099/00207713-49-3-1025" class="text-muted" target="_blank" rel="noopener noreferrer">10.1099/00207713-49-3-1025<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1371/journal.pone.0102963" target="_blank" rel="noopener noreferrer" class="name">High-Throughput Sequencing and De Novo Assembly of the Isatis indigotica Transcriptome<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2014-09-26">September 2014</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Tang, Xiaoqing; Xiao, Yunhua; Lv, Tingting</span> </li> <li> PLoS ONE, Vol. 9, Issue 9</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1371/journal.pone.0102963" class="text-muted" target="_blank" rel="noopener noreferrer">10.1371/journal.pone.0102963<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1099/mic.0.080705-0" target="_blank" rel="noopener noreferrer" class="name">A cAMP-independent carbohydrate-driven mechanism inhibits tnaA expression and TnaA enzyme activity in Escherichia coli<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2014-07-24">July 2014</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Li, G.; Young, K. D.</span> </li> <li> Microbiology, Vol. 160, Issue Pt_9</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1099/mic.0.080705-0" class="text-muted" target="_blank" rel="noopener noreferrer">10.1099/mic.0.080705-0<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1038/sj.jim.7000228" target="_blank" rel="noopener noreferrer" class="name">Application of metabolic engineering to improve both the production and use of biotech indigo<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2002-03-01">March 2002</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Berry, A.; Dodge, Tc; Pepsin, M.</span> </li> <li> Journal of Industrial Microbiology and Biotechnology, Vol. 28, Issue 3</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1038/sj.jim.7000228" class="text-muted" target="_blank" rel="noopener noreferrer">10.1038/sj.jim.7000228<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1107/S0021889807021206" target="_blank" rel="noopener noreferrer" class="name"><em>Phaser</em> crystallographic software<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2007-07-13">July 2007</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D.</span> </li> <li> Journal of Applied Crystallography, Vol. 40, Issue 4</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1107/S0021889807021206" class="text-muted" target="_blank" rel="noopener noreferrer">10.1107/S0021889807021206<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1111/j.1478-4408.2009.00197.x" target="_blank" rel="noopener noreferrer" class="name">The development of indigo reduction methods and pre-reduced indigo products: Indigo reduction methods and pre-reduced indigo products<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2009-08-01">August 2009</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Blackburn, Richard S.; Bechtold, Thomas; John, Philip</span> </li> <li> Coloration Technology, Vol. 125, Issue 4</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1111/j.1478-4408.2009.00197.x" class="text-muted" target="_blank" rel="noopener noreferrer">10.1111/j.1478-4408.2009.00197.x<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> <div> <h2 class="title" style="margin-bottom:0;" data-apporder=""> <a href="https://doi.org/10.1023/A:1011948405581" target="_blank" rel="noopener noreferrer" class="name">Production and characterization of β-glucosidases from different Aspergillus strains<span class="fa fa-external-link" aria-hidden="true"></span></a> <small class="text-muted" style="text-transform:uppercase; font-size:0.75rem;"><br/> <span class="type">journal</span>, <span class="date" data-date="2001-07-01">July 2001</span></small> </h2> <ul class="small references-list" style="list-style-type:none; margin-top: 0.5em; padding-left: 0; line-height:1.8em;"> <li> <span style="color:#7cb342;"> Jäger, Szilvia; Brumbauer, Anikó; Fehér, Erika</span> </li> <li> World Journal of Microbiology and Biotechnology, Vol. 17, Issue 5</li> <li> <span class="text-muted related-url">DOI: <a href="https://doi.org/10.1023/A:1011948405581" class="text-muted" target="_blank" rel="noopener noreferrer">10.1023/A:1011948405581<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> <hr/> </div> </div> <div class="pagination-container small"> <a class="pure-button prev page" href="#" rel="prev"><span class="fa fa-angle-left"></span></a><ul class="pagination d-inline-block" style="padding-left:.2em;"></ul><a class="pure-button next page" href="#" rel="next"><span class="fa fa-angle-right"></span></a> </div> </div> </div> <div class="col-sm-3 order-sm-3"> <ul class="nav nav-stacked"> <li class="active"><a href="" class="reference-type-filter tab-nav" data-tab="biblio-references" data-filter="type" data-pattern="*"><span class="fa fa-angle-right"></span> All References</a></li> <li class="small" style="margin-left:.75em; 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float:none;">[ × clear filter / sort ]</a> </div> </form> </div> </div> </div> </section> <section id="biblio-images" class="tab-content tab-content-sec osti-curated" data-tab="biblio"> <div class="row"> <div class="col-sm-9 order-sm-9"> <div class="padding"> <p class="lead text-muted" style="font-size: 18px; margin-top:0px;"><span id="image-type-label">Figures / Tables</span> found in this record:</p> <div class="list clearfix"> <div class="col-sm-3 float-left biblio-image-tile" data-apporder="p. 21" data-order="1" data-imgid="1485082-img87170" data-imgsrc="/biblio/1485082/image/000/125/0001256/3/0087170.png" data-title="Figure 1" data-desc="A glucosyl protecting group enables control over the timing and location of indigo dyeing" data-ostiid="1485082" style="padding-bottom: 2em; border-bottom: 1px solid #ddd;"> <a href="#img" class="biblio-image-tile-a ga-click-event" data-imgid="1485082-img87170" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87170"> <div style=" padding: .5em; border: 1px solid #eee; background-color: #fff; "> <small class="name">Figure 1 <small class="pull-right" style="margin-right: .5em;color:#999;top: 3px;position: relative;">(p. 21)</small><span class="d-none type">figure</span></small> <div style=" background-image:url('/biblio/1485082/image/000/125/0001256/3/t0087170.png'); background-repeat:no-repeat; background-size:contain; background-position-x: center; width: 100%; height: 175px; margin-top:.5em; "> </div> </div> </a> </div> <div class="col-sm-3 float-left biblio-image-tile" data-apporder="p. 22" data-order="2" data-imgid="1485082-img87172" data-imgsrc="/biblio/1485082/image/000/125/0001256/3/0087172.png" data-title="Figure 2" data-desc="The crystal structure of PtUGT1 with bound indoxyl sulfate (a) Overall GT-B fold of PtUGT1 (PDB ID 5NLM). The N-terminal Rossmann domain (blue) consists of a seven-stranded parallel β-sheet surrounded by nine α-helical segments, and the C-terminal Rossmann domain (red) consists of a six-stranded parallel β-sheet and five α-helices. The indoxyl sulfate bound in the active site is shown in stick representation. The structure is annotated with the four amino acids differing between PtUGT1 and PtUGT2 (arrows). (b) Electrostatic surface potential of PtUGT1. Colors show the electrostatic potential, from −5 $kT/e$ (red) to 5 $kT/e$ (blue). The view is rotated ~90° around the x axis with respect to a. Bound indoxyl sulfate is depicted in stick representation (black) together with the donor substrate UDP-glucose superposed from the homologous AtUGT72B1 complex structure (cyan, PDB ID 2VCE). (c) The acceptor binding site with the bound indoxyl sulfate and interacting residues shown in stick representation. The indoxyl sulfate omit map is displayed as a blue grid contoured at 3.0 σ. Interactions are depicted as dashed lines (black, salt bridge/hydrogen bond; gray, hydrophobic interaction; yellow, π-stacking). A black solid line indicates the distance from the catalytic histidine to the glucose-accepting oxygen. (d) In the proposed catalytic mechanism based on homology to other characterized UGTs29,31, H26 deprotonates the indoxyl hydroxyl group, which then performs an SN2 attack on the anomeric carbon of glucose. The conserved D122 is believed to balance the charge on the catalytic histidine29. Consistent with this hypothesis, D122 forms a 2.6 Å hydrogen bond to H26 in the present structure." data-ostiid="1485082" style="padding-bottom: 2em; border-bottom: 1px solid #ddd;"> <a href="#img" class="biblio-image-tile-a ga-click-event" data-imgid="1485082-img87172" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87172"> <div style=" padding: .5em; border: 1px solid #eee; background-color: #fff; "> <small class="name">Figure 2 <small class="pull-right" style="margin-right: .5em;color:#999;top: 3px;position: relative;">(p. 22)</small><span class="d-none type">figure</span></small> <div style=" background-image:url('/biblio/1485082/image/000/125/0001256/3/t0087172.png'); background-repeat:no-repeat; background-size:contain; background-position-x: center; width: 100%; height: 175px; margin-top:.5em; "> </div> </div> </a> </div> <div class="col-sm-3 float-left biblio-image-tile" data-apporder="p. 23" data-order="3" data-imgid="1485082-img87173" data-imgsrc="/biblio/1485082/image/000/125/0001256/3/0087173.png" data-title="Figure 3" data-desc="Heterologous expression of PtUGT1 stabilizes indoxyl before it dimerizes, producing indican (a) Tryptophan is converted to indole by the native E. coli enzyme TnaA, oxygenated to indoxyl by FMO, and glucosylated by PtUGT1. A β-glucosidase hydrolyzes indican into indoxyl, which spontaneously oxidizes to indigo. (b) Expression of PtUGT1 reduces indigo formation in an FMO-expressing ΔbglA strain, but indigo precipitate forms upon addition of β-glucosidase. (c) Indican can be produced in a ΔbglA strain by heterologous expression of both FMO and PtUGT1, and titers improve with exogenous feeding of more tryptophan than the 20 mg/L present in EZ Rich media. Bars represent the mean of four biological replicates, and each replicate is represented by a circle." data-ostiid="1485082" style="padding-bottom: 2em; border-bottom: 1px solid #ddd;"> <a href="#img" class="biblio-image-tile-a ga-click-event" data-imgid="1485082-img87173" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87173"> <div style=" padding: .5em; border: 1px solid #eee; background-color: #fff; "> <small class="name">Figure 3 <small class="pull-right" style="margin-right: .5em;color:#999;top: 3px;position: relative;">(p. 23)</small><span class="d-none type">figure</span></small> <div style=" background-image:url('/biblio/1485082/image/000/125/0001256/3/t0087173.png'); background-repeat:no-repeat; background-size:contain; background-position-x: center; width: 100%; height: 175px; margin-top:.5em; "> </div> </div> </a> </div> <div class="col-sm-3 float-left biblio-image-tile" data-apporder="p. 24" data-order="4" data-imgid="1485082-img87175" data-imgsrc="/biblio/1485082/image/000/125/0001256/3/0087175.png" data-title="Figure 4" data-desc="Production and growth curves for indican and indigo production (a–d) Titers of indican (a), indigo (b), and tryptophan (c), and cell count (d; measured as colony-forming units (CFU), see “Determination of cell count” in Online Methods) over a 37 h growth period. Cells expressing FMO and PtUGT1 are represented by orange; cells expressing only FMO are represented by blue; cells expressing neither gene are represented by gray. Error bars represent the mean ± s.d. of six (FMO + UGT) or four (FMO) independently grown colonies; circles represent individual independently grown colonies." data-ostiid="1485082" style="padding-bottom: 2em; border-bottom: 1px solid #ddd;"> <a href="#img" class="biblio-image-tile-a ga-click-event" data-imgid="1485082-img87175" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87175"> <div style=" padding: .5em; border: 1px solid #eee; background-color: #fff; "> <small class="name">Figure 4 <small class="pull-right" style="margin-right: .5em;color:#999;top: 3px;position: relative;">(p. 24)</small><span class="d-none type">figure</span></small> <div style=" background-image:url('/biblio/1485082/image/000/125/0001256/3/t0087175.png'); background-repeat:no-repeat; background-size:contain; background-position-x: center; width: 100%; height: 175px; margin-top:.5em; "> </div> </div> </a> </div> <div class="col-sm-3 float-left biblio-image-tile" data-apporder="p. 25" data-order="5" data-imgid="1485082-img87176" data-imgsrc="/biblio/1485082/image/000/125/0001256/3/0087176.png" data-title="Figure 5" data-desc="Bio-indican can be used as an effective, reductant-free cotton textile dye (a) Top row, Pure indican with no β-glucosidase (BGL); pure indican with β-glucosidase; bio-indican with β-glucosidase. Bottom row, Indigo, nonreduced; indigo, reduced with sodium dithionite. All swatches are dyed on white cotton denim. Scale bar, 1 cm. (b) Scarf (100% white cotton gauze fabric) dyed with indican. All samples were photographed after numerous, vigorous water washes. Scale bar, 5 cm." data-ostiid="1485082" style="padding-bottom: 2em; border-bottom: 1px solid #ddd;"> <a href="#img" class="biblio-image-tile-a ga-click-event" data-imgid="1485082-img87176" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87176"> <div style=" padding: .5em; border: 1px solid #eee; background-color: #fff; "> <small class="name">Figure 5 <small class="pull-right" style="margin-right: .5em;color:#999;top: 3px;position: relative;">(p. 25)</small><span class="d-none type">figure</span></small> <div style=" background-image:url('/biblio/1485082/image/000/125/0001256/3/t0087176.png'); background-repeat:no-repeat; background-size:contain; background-position-x: center; width: 100%; height: 175px; margin-top:.5em; "> </div> </div> </a> </div> </div> <div class="pagination-container small"> <a class="pure-button prev page" href="#" rel="prev"><span class="fa fa-angle-left"></span></a><ul class="pagination d-inline-block" style="padding-left:.2em;"></ul><a class="pure-button next page" href="#" rel="next"><span class="fa fa-angle-right"></span></a> </div> </div> </div> <div class="col-sm-3 order-sm-3"> <ul class="nav nav-stacked"> <li class="active"><a href="" class="reference-type-filter tab-nav" data-tab="biblio-images" data-filter="type" data-pattern="*"><span class="fa fa-angle-right"></span> All Images</a></li> <li class="small" style="margin-left:.75em; text-transform:capitalize;"><a href="" class="reference-type-filter tab-nav ga-click-event" data-tab="biblio-images" data-filter="type" data-pattern="figure" data-category="Extracted Images" data-label="biblio: image filter - figure"><span class="fa fa-angle-right"></span> figures<small class="text-muted"> (5)</small></a></li> </ul> <div style="margin-top:2em;"> <form class="pure-form small text-muted image-search"> <label for="image-search-text" class="sr-only">Search</label> <input class="search form-control pure-input-1" id="image-search-text" placeholder="Search" style="margin-bottom:10px;" /> <fieldset> <div style="margin-left:1em; font-weight:normal; line-height: 1.6em;"><input type="radio" class="sort ga-click-event" name="images-sort" data-sort="name" style="position:relative;top:2px;" id="image-search-sort-name" data-category="Extracted Images" data-label="biblio: image sort - name"><label for="image-search-sort-name" style="margin-left: .3em;">Sort by figure / table title</label></div> <div style="margin-left:1em; font-weight:normal; line-height: 1.6em;"><input type="radio" class="sort ga-click-event" name="images-sort" data-sort="order" style="position:relative;top:2px;" id="image-search-sort-date" data-category="Extracted Images" data-label="biblio: image sort - order"><label for="image-search-sort-date" style="margin-left: .3em;">Sort by page order</label></div> </fieldset> <div class="text-left" style="margin-top:1.5em;margin-left:1em;"> <a href="" class="filter-clear clearfix" title="Clear filter / sort" style="font-weight:normal; float:none;">[ × clear filter / sort ]</a> </div> </form> </div> <div class="text-muted small" style="margin-top:2em; padding:1em;"> <em>Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.</em> </div> </div> </div> </section> <section id="biblio-related" class="tab-content tab-content-sec " data-tab="biblio"> <div class="row"> <div class="col-sm-9 order-sm-9"> <section id="biblio-similar" class="tab-content tab-content-sec active" data-tab="related"> <div class="padding"> <p class="lead text-muted" style="font-size: 18px; margin-top:0px;">Similar records in OSTI.GOV collections:</p> <aside> <ul class="item-list" itemscope itemtype="http://schema.org/ItemList" style="padding-left:0; list-style-type: none;"> <li> <div class="article item document" itemprop="itemListElement" itemscope itemtype="http://schema.org/WebPage"><meta itemprop="position" content="4" /><div class="item-info"> <h2 class="title" itemprop="name headline"><a href="/biblio/10125611-community-geothermal-technology-program-cloth-dyeing-geothermal-steam-experiment-technology-transfer-from-japan-hawaii-final-report" itemprop="url">Community Geothermal Technology Program: Cloth dyeing by geothermal steam. An experiment in technology transfer from Japan to Hawaii, Final report</a></h2> <div class="metadata"> <small class="text-muted" style="text-transform:uppercase;display:block;line-height:2.5em;">Technical Report</small><span class="authors"> <span class="author">Furumoto, A.S.</span> <span class="text-muted pubdata"></span> </span> </div> <div class="abstract">This was an experiment to test whether cloth dyeing using geothermal steam (already proven in Japan) would be feasible in Hawaii. Results: Using a fabricated steam vat, cotton, silk, and synthetic can be dyed; the resulting material received high grades for steadfastness and permanency under dye testing. Techniques that were successful in Matsukawa, were replicated in Puna. However, attempts to embed leaf patterns on cloth using natural leaves and to extract natural dyes from Hawaiian plants were unsuccessful; the color of natural dyes deteriorated in hours. But chemical dyes gave brilliant hues or shades, in contrast to those in Japan<a href='#' onclick='$(this).hide().next().show().next().show();return false;' style='margin-left:10px;'>more »</a><span style='display:none;'> where the steam there gave subdued tones. It is concluded that geothermal dyeing can be a viable cottage industry in Puna, Hawaii.</span><a href='#' onclick='$(this).hide().prev().hide().prev().show();return false;' style='margin-left:10px;display:none;'>« less</a></div><div class="metadata-links small clearfix text-muted" style="margin-top:15px;"> <div class="pure-menu pure-menu-horizontal pull-right" style="width:unset;"> <ul class="pure-menu-list"> <li class="pure-menu-item"><span class="item-info-ftlink">DOI: <a class="misc doi-link " href="https://doi.org/10.2172/10125611" target="_blank" rel="noopener" title="Link to document DOI" data-ostiid="10125611" data-product-type="Technical Report" data-product-subtype="" >10.2172/10125611</a></span></li> <li class="pure-menu-item"><span class="item-info-ftlink"><a class="misc fulltext-link " href="/servlets/purl/10125611" title="Link to document media" target="_blank" rel="noopener" data-ostiid="10125611" data-product-type="Technical Report" data-product-subtype="" >Full Text Available</a></span></li> </ul> </div> </div> </div> <div class="clearfix"></div> </div> </li> </ul> </aside> </div> </section> </div> <div class="col-sm-3 order-sm-3"> <ul class="nav nav-stacked"> <li class="active"><a class="tab-nav disabled" data-tab="related" style="color: #636c72 !important; opacity: 1;"><span class="fa fa-angle-right"></span> Similar Records</a></li> </ul> </div> </div> </section> </div></div> </div> </div> </section> <footer class="" style="background-color:#f9f9f9; /* padding-top: 0.5rem; */"> <div class="footer-minor"> <div class="container"> <hr class="footer-separator" /> <div class="text-center" style="margin-top:1.25rem;"> <div class="pure-menu pure-menu-horizontal"> <ul class="pure-menu-list" id="footer-org-menu"> <li class="pure-menu-item d-block d-inline-small"> <a href="https://energy.gov" target="_blank" rel="noopener noreferrer"> <img src="data:image/gif;base64,R0lGODlhAQABAIAAAP///wAAACH5BAEAAAAALAAAAAABAAEAAAICRAEAOw==" class="sprite sprite-footer-us-doe-min" alt="U.S. Department of Energy" /> </a> </li> <li class="pure-menu-item d-block d-inline-small"> <a href="https://www.energy.gov/science/office-science" target="_blank" rel="noopener noreferrer"> <img src="data:image/gif;base64,R0lGODlhAQABAIAAAP///wAAACH5BAEAAAAALAAAAAABAAEAAAICRAEAOw==" class="sprite sprite-footer-office-of-science-min" alt="Office of Science" /> </a> </li> <li class="pure-menu-item d-block d-inline-small"> <a href="/"> <img src="data:image/gif;base64,R0lGODlhAQABAIAAAP///wAAACH5BAEAAAAALAAAAAABAAEAAAICRAEAOw==" class="sprite sprite-footer-osti-min" alt="Office of Scientific and Technical Information" /> </a> </li> </ul> </div> </div> <div class="text-center small" style="margin-top:0.5em;margin-bottom:2.0rem;"> <div class="pure-menu pure-menu-horizontal"> <ul class="pure-menu-list"> <li class="pure-menu-item"><a href="/disclaim" class="pure-menu-link"><span class="fa fa-institution"></span> Website Policies <span class="d-none d-sm-inline" style="color:#737373;">/ Important Links</span></a></li> <li class="pure-menu-item"><a href="/contact" class="pure-menu-link"><span class="fa fa-comments-o"></span> Contact Us</a></li> <li class="d-block d-md-none mb-1"></li> <li class="pure-menu-item"><a href="https://www.facebook.com/ostigov" target="_blank" rel="noopener noreferrer" class="pure-menu-link social"><span class="fa fa-facebook" style=""></span></a></li> <li class="pure-menu-item"><a href="https://twitter.com/OSTIgov" target="_blank" rel="noopener noreferrer" class="pure-menu-link social"><span class="fa fa-twitter" style=""></span></a></li> <li class="pure-menu-item"><a href="https://www.youtube.com/user/ostigov" target="_blank" rel="noopener noreferrer" class="pure-menu-link social"><span class="fa fa-youtube-play" style=""></span></a></li> </ul> </div> </div> </div> </div> </footer> <link href="/css/ostigov.fonts.191107.1502.css" rel="stylesheet"> <script src="/js/ostigov.191107.1502.js"></script><noscript></noscript> <script defer src="/js/ostigov.biblio.191107.1502.js"></script><noscript></noscript> <script defer src="/js/lity.js"></script><noscript></noscript> <script async type="text/javascript" src="/js/Universal-Federated-Analytics-Min.js?agency=DOE" id="_fed_an_ua_tag"></script><noscript></noscript> </body> <!-- OSTI.GOV v.191107.1502 --> </html>