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

Journal Article · · Nature Chemical Biology
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
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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.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1485082
Journal Information:
Nature Chemical Biology, Vol. 14, Issue 3; ISSN 1552-4450
Publisher:
Nature Publishing GroupCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 95 works
Citation information provided by
Web of Science

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Joachim</li> <li class="mb-0-5 source"> <span class="mr-1">figshare</span> <span class="text-muted"><a href="https://doi.org/10.6084/m9.figshare.1408441" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.6084/m9.figshare.1408441<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="image">image</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2015-01-01">January 2015</span></td> </tr></tbody></table> </div> </div> </section> <hr class="mt-2 mb-2"/> <section id="section-citations" data-list="list_cite" class="tab-content-sec osti-curated biblio-section section-scroll" style="scroll-margin-top:110px;"> <div class="biblio-section-navbar active row"> <div class="col"> <h2 class="abstract biblio-section-title mt-0 mb-0-5" style="cursor:pointer;"><span class="fa indicator"></span> Cited By (20) <span class="text-muted list-table-filternum"></span></h2> </div> <div class="col-md-12 col-lg-auto"> <form class="pure-form reference-filter d-print-none"> <div class="small biblio-section-navbar-tool"> <label for="list-table-search-citations" class="sr-only">Search citations: </label> <input type="text" class="list-table-search mt-0 mb-0-5 ml-1" id="list-table-search-citations" placeholder="Search citations ..."> </div> <div class="small biblio-section-navbar-tool"> <select class="list-table-type mt-0 mb-0-5"> <option value="">Resource Types</option> <option value="journal">Journal</option><option value="text">Text</option> </select> </div> <div class="small biblio-section-navbar-tool"> <select class="list-table-sort mt-0 mb-0-5"> <option value="date">Sort by Date</option> <option value="title">Sort by Title</option> </select> </div> <div class="small biblio-section-navbar-tool"> <button type="reset" class="pure-button list-table-reset mt-0 mb-0-5">↺</button> </div> </form> </div> </div> <div class="row"> <div class="col-sm-12"> <table id="list-table-citations" class="truncate-rows list-table table-striped" data-rows="5" style="width:100%;"><tbody class="list"><tr> <td> <a href="https://doi.org/10.1002/bit.26934" target="_blank" rel="noopener noreferrer" class="title" data-title="Decoupling of recombinant protein production from emEscherichia coliem cell growth enhances functional expression of plant Leloir glycosyltransferases">Decoupling of recombinant protein production from <em>Escherichia coli</em> cell growth enhances functional expression of plant Leloir glycosyltransferases<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; 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padding-left: 0; line-height:1.8em;"> <li class="authors">Wehrs, Maren; Gladden, John M.; Liu, Yuzhong</li> <li class="mb-0-5 source"> <span class="mr-1">Green Chemistry, Vol. 21, Issue 12</span> <span class="text-muted"><a href="https://doi.org/10.1039/c9gc00920e" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1039/c9gc00920e<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-01-01">January 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1080/10286020.2019.1642330" target="_blank" rel="noopener noreferrer" class="title" data-title="Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from emTripterygium wilfordiiem">Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from <em>Tripterygium wilfordii</em><span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Lu, Yun; Ma, Bao-Wei; Gao, Jie</li> <li class="mb-0-5 source"> <span class="mr-1">Journal of Asian Natural Products Research, Vol. 22, Issue 6</span> <span class="text-muted"><a href="https://doi.org/10.1080/10286020.2019.1642330" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1080/10286020.2019.1642330<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-07-24">July 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1093/jxb/ery305" target="_blank" rel="noopener noreferrer" class="title" data-title="A novel glycosyltransferase catalyses the transfer of glucose to glucosylated anthocyanins in purple sweet potato">A novel glycosyltransferase catalyses the transfer of glucose to glucosylated anthocyanins in purple sweet potato<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Wang, Hongxia; Wang, Chengyuan; Fan, Weijuan</li> <li class="mb-0-5 source"> <span class="mr-1">Journal of Experimental Botany</span> <span class="text-muted"><a href="https://doi.org/10.1093/jxb/ery305" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1093/jxb/ery305<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2018-08-17">August 2018</span></td> </tr><tr> <td> <a href="https://doi.org/10.1111/tpj.14321" target="_blank" rel="noopener noreferrer" class="title" data-title="Crystal structures of rhamnosyltransferase scpUGTscp 89C1 from emArabidopsis thalianaem reveal the molecular basis of sugar donor specificity for scpUDPscp scplscp rhamnose and rhamnosylation mechanism">Crystal structures of rhamnosyltransferase <scp>UGT</scp> 89C1 from <em>Arabidopsis thaliana</em> reveal the molecular basis of sugar donor specificity for <scp>UDP</scp> ‐β‐ <scp>l</scp> ‐rhamnose and rhamnosylation mechanism<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Zong, Guangning; Fei, Shuang; Liu, Xiao</li> <li class="mb-0-5 source"> <span class="mr-1">The Plant Journal</span> <span class="text-muted"><a href="https://doi.org/10.1111/tpj.14321" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1111/tpj.14321<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-04-22">April 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1111/tpj.14514" target="_blank" rel="noopener noreferrer" class="title" data-title="Phylogenomic analysis of UDPdependent glycosyltransferases provides insights into the evolutionary landscape of glycosylation in plant metabolism">Phylogenomic analysis of UDP‐dependent glycosyltransferases provides insights into the evolutionary landscape of glycosylation in plant metabolism<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Wilson, Alexander E.; Tian, Li</li> <li class="mb-0-5 source"> <span class="mr-1">The Plant Journal, Vol. 100, Issue 6</span> <span class="text-muted"><a href="https://doi.org/10.1111/tpj.14514" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1111/tpj.14514<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-10-06">October 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1515/hsz-2019-0109" target="_blank" rel="noopener noreferrer" class="title" data-title="Indigoid dyes by group E monooxygenases mechanism and biocatalysis">Indigoid dyes by group E monooxygenases: mechanism and biocatalysis<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Heine, Thomas; Großmann, Carolin; Hofmann, Sarah</li> <li class="mb-0-5 source"> <span class="mr-1">Biological Chemistry, Vol. 400, Issue 7</span> <span class="text-muted"><a href="https://doi.org/10.1515/hsz-2019-0109" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1515/hsz-2019-0109<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-06-26">June 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.3389/fchem.2019.00278" target="_blank" rel="noopener noreferrer" class="title" data-title="Flavin Conjugated Polydopamine Nanoparticles Displaying LightDriven Monooxygenase Activity">Flavin Conjugated Polydopamine Nanoparticles Displaying Light-Driven Monooxygenase Activity<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Crocker, Leander; Fruk, Ljiljana</li> <li class="mb-0-5 source"> <span class="mr-1">Frontiers in Chemistry, Vol. 7</span> <span class="text-muted"><a href="https://doi.org/10.3389/fchem.2019.00278" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.3389/fchem.2019.00278<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-04-26">April 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1002/cbic.201900400" target="_blank" rel="noopener noreferrer" class="title" data-title="Cellular Biocatalysts Using Synthetic Genetic Circuits for Prolonged and Durable Enzymatic Activity">Cellular Biocatalysts Using Synthetic Genetic Circuits for Prolonged and Durable Enzymatic Activity<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Ahan, Recep Erdem; Saltepe, Behide; Apaydin, Onur</li> <li class="mb-0-5 source"> <span class="mr-1">ChemBioChem</span> <span class="text-muted"><a href="https://doi.org/10.1002/cbic.201900400" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1002/cbic.201900400<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-07-02">July 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.6084/m9.figshare.9033980" target="_blank" rel="noopener noreferrer" class="title" data-title="Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from iTripterygium wilfordiii">Isolation and characterization of a glycosyltransferase with specific catalytic activity towards flavonoids from <i>Tripterygium wilfordii</i><span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Lu, Yun; Ma, Bao-Wei; Gao, Jie</li> <li class="mb-0-5 source"> <span class="mr-1">Taylor & Francis</span> <span class="text-muted"><a href="https://doi.org/10.6084/m9.figshare.9033980" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.6084/m9.figshare.9033980<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="text">text</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-01-01">January 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.17863/cam.39949" target="_blank" rel="noopener noreferrer" class="title" data-title="Flavin Conjugated Polydopamine Nanoparticles Displaying LightDriven Monooxygenase Activity">Flavin Conjugated Polydopamine Nanoparticles Displaying Light-Driven Monooxygenase Activity.<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Crocker, Leander; Fruk, Ljiljana</li> <li class="mb-0-5 source"> <span class="mr-1">Apollo - University of Cambridge Repository</span> <span class="text-muted"><a href="https://doi.org/10.17863/cam.39949" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.17863/cam.39949<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="text">text</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2019-01-01">January 2019</span></td> </tr><tr> <td> <a href="https://doi.org/10.1021/acssynbio.8b00377" target="_blank" rel="noopener noreferrer" class="title" data-title="Designing Spatially Distributed Gene Regulatory Networks To Elicit Contrasting Patterns">Designing Spatially Distributed Gene Regulatory Networks To Elicit Contrasting Patterns<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Tei, Mika; Perkins, Melinda Liu; Hsia, Justin</li> <li class="mb-0-5 source"> <span class="mr-1">ACS Synthetic Biology, Vol. 8, Issue 1</span> <span class="text-muted"><a href="https://doi.org/10.1021/acssynbio.8b00377" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.1021/acssynbio.8b00377<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2018-12-12">December 2018</span></td> </tr><tr> <td> <a href="https://doi.org/10.3389/fmicb.2018.02625" target="_blank" rel="noopener noreferrer" class="title" data-title="Biodegradation and Biotransformation of Indole Advances and Perspectives">Biodegradation and Biotransformation of Indole: Advances and Perspectives<span class="fa fa-external-link" aria-hidden="true"></span></a> <ul class="small references-list mb-0 mt-0" style="list-style-type:none; padding-left: 0; line-height:1.8em;"> <li class="authors">Ma, Qiao; Zhang, Xuwang; Qu, Yuanyuan</li> <li class="mb-0-5 source"> <span class="mr-1">Frontiers in Microbiology, Vol. 9</span> <span class="text-muted"><a href="https://doi.org/10.3389/fmicb.2018.02625" class="text-muted" target="_blank" rel="noopener noreferrer">https://doi.org/10.3389/fmicb.2018.02625<span class="fa fa-external-link" aria-hidden="true"></span></a></span> </li> </ul> </td> <td class="small text-muted biblio-refs-td-secondary"> <span class="biblio-refs-type-badge ml-1 type" data-type="journal">journal</span> </td> <td class="small text-muted biblio-refs-td-secondary biblio-refs-td-secondary-date"><span class="date" data-date="2018-11-01">November 2018</span></td> </tr></tbody></table> </div> </div> </section> <hr class="mt-2 mb-2"/> <section id="section-images" data-list="list_img" class="tab-content-sec osti-curated biblio-section section-scroll" style="scroll-margin-top:110px;"> <div class="biblio-section-navbar active row"> <div class="col"> <h2 class="abstract biblio-section-title mt-0 mb-0-5" style="cursor:pointer;"><span class="fa indicator"></span> Figures / Tables (5) <span class="text-muted list-table-filternum"></span></h2> </div> <div class="col-md-12 col-lg-auto"> <form class="pure-form reference-filter d-print-none"> <div class="small biblio-section-navbar-tool"> <label for="list-table-search-figures" class="sr-only">Search figures / tables: </label> <input type="text" class="list-table-search mt-0 mb-0-5 ml-1" id="list-table-search-figures" placeholder="Search figures / tables ..."> </div> <div class="small biblio-section-navbar-tool"> <select class="list-table-sort mt-0 mb-0-5"> <option value="date">Sort by Date</option> <option value="title">Sort by Title</option> </select> </div> <div class="small biblio-section-navbar-tool"> <button type="reset" class="pure-button list-table-reset mt-0 mb-0-5">↺</button> </div> </form> </div> </div> <div class="row"> <div class="col-sm-12"> <table id="list-table-images" class="truncate-rows list-table list-table-images table-to-tiles" data-rows="1" style="width:100%;"><tbody class="list"> <tr class="biblio-image-tile "><td class="col-sm-3"> <a id="img-1485082-img87170" data-pos="first" href="#modal-image" data-modal-toggle="true" class="biblio-image-tile-a ga-click-event apporder order title desc" data-imgid="1485082-img87170" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87170" 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="<strong>A glucosyl protecting group enables control over the timing and location of indigo dyeing</strong>" data-ostiid="1485082"> <div class="biblio-image-tile-inner"> <small class="name">Figure 1<small class="pull-right text-muted" style="margin-right: .5em;top: 3px;position: relative;">(p. 21)</small><span class="d-none type">figure</span></small> <img class="img-responsive mt-0-5" alt="Figure 1" src="/biblio/1485082/image/000/125/0001256/3/t0087170.png"/> </div> </a> </td></tr> <tr class="biblio-image-tile "><td class="col-sm-3"> <a id="img-1485082-img87172" data-pos="" href="#modal-image" data-modal-toggle="true" class="biblio-image-tile-a ga-click-event apporder order title desc" data-imgid="1485082-img87172" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87172" 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="<strong>The crystal structure of PtUGT1 with bound indoxyl sulfate</strong> <strong>(a)</strong> 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). <strong>(b) </strong>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). <strong>(c)</strong> 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, <strong>π</strong>-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 UGTs<sup>29,31</sup>, H26 deprotonates the indoxyl hydroxyl group, which then performs an S<sub>N</sub>2 attack on the anomeric carbon of glucose. The conserved D122 is believed to balance the charge on the catalytic histidine<sup>29</sup>. Consistent with this hypothesis, D122 forms a 2.6 Å hydrogen bond to H26 in the present structure." data-ostiid="1485082"> <div class="biblio-image-tile-inner"> <small class="name">Figure 2<small class="pull-right text-muted" style="margin-right: .5em;top: 3px;position: relative;">(p. 22)</small><span class="d-none type">figure</span></small> <img class="img-responsive mt-0-5" alt="Figure 2" src="/biblio/1485082/image/000/125/0001256/3/t0087172.png"/> </div> </a> </td></tr> <tr class="biblio-image-tile "><td class="col-sm-3"> <a id="img-1485082-img87173" data-pos="" href="#modal-image" data-modal-toggle="true" class="biblio-image-tile-a ga-click-event apporder order title desc" data-imgid="1485082-img87173" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87173" 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="<strong>Heterologous expression of PtUGT1 stabilizes indoxyl before it dimerizes, producing indican (a)</strong> Tryptophan is converted to indole by the native <em>E. coli</em> enzyme TnaA, oxygenated to indoxyl by FMO, and glucosylated by PtUGT1. A β-glucosidase hydrolyzes indican into indoxyl, which spontaneously oxidizes to indigo. <strong>(b)</strong> Expression of PtUGT1 reduces indigo formation in an FMO-expressing<em> ΔbglA</em> strain, but indigo precipitate forms upon addition of β-glucosidase. <strong>(c)</strong> Indican can be produced in a <em>ΔbglA</em> 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"> <div class="biblio-image-tile-inner"> <small class="name">Figure 3<small class="pull-right text-muted" style="margin-right: .5em;top: 3px;position: relative;">(p. 23)</small><span class="d-none type">figure</span></small> <img class="img-responsive mt-0-5" alt="Figure 3" src="/biblio/1485082/image/000/125/0001256/3/t0087173.png"/> </div> </a> </td></tr> <tr class="biblio-image-tile "><td class="col-sm-3"> <a id="img-1485082-img87175" data-pos="" href="#modal-image" data-modal-toggle="true" class="biblio-image-tile-a ga-click-event apporder order title desc" data-imgid="1485082-img87175" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87175" 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="<strong>Production and growth curves for indican and indigo production (a–d)</strong> Titers of indican <strong>(a)</strong>, indigo <strong>(b)</strong>, and tryptophan <strong>(c)</strong>, and cell count (<strong>d</strong>; 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"> <div class="biblio-image-tile-inner"> <small class="name">Figure 4<small class="pull-right text-muted" style="margin-right: .5em;top: 3px;position: relative;">(p. 24)</small><span class="d-none type">figure</span></small> <img class="img-responsive mt-0-5" alt="Figure 4" src="/biblio/1485082/image/000/125/0001256/3/t0087175.png"/> </div> </a> </td></tr> <tr class="biblio-image-tile tr-striped"><td class="col-sm-3"> <a id="img-1485082-img87176" data-pos="last" href="#modal-image" data-modal-toggle="true" class="biblio-image-tile-a ga-click-event apporder order title desc" data-imgid="1485082-img87176" data-lityx data-category="Extracted Images" data-label="biblio: image thumbnail" data-value="1485082-img87176" 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="<strong>Bio-indican can be used as an effective, reductant-free cotton textile dye (a)</strong> 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. <strong>(b)</strong> 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"> <div class="biblio-image-tile-inner"> <small class="name">Figure 5<small class="pull-right text-muted" style="margin-right: .5em;top: 3px;position: relative;">(p. 25)</small><span class="d-none type">figure</span></small> <img class="img-responsive mt-0-5" alt="Figure 5" src="/biblio/1485082/image/000/125/0001256/3/t0087176.png"/> </div> </a> </td></tr> </tbody></table> </div> </div> </section> <div id="modal-image" class="modal"> <div class="modal-content"> <div class="modal-header"> <span class="close" data-modal-close="true">×</span> <header id="modal-image_label" style="margin:0px;">Image title</header> </div> <div id="modal-image_body" class="modal-body"> </div> </div> </div> <hr class="mt-2 mb-2"/> <section id="section-similar" class="tab-content-sec osti-curated biblio-section section-scroll" style="scroll-margin-top:110px;"> <div class="row"> <div class="col-8" style="padding-right:40px;"> <h2 class="abstract">Similar Records</h2> <div class="" style="line-height:1.6rem;"> <a href="/biblio/22788359" target="_blank">Fastness Properties and Color Analysis of Natural Indigo Dye and Compatibility Study of Different Natural Reducing Agents</a> <div class="small" style="line-height:1.4rem;"> Journal Article <span style="padding-left: 0.75rem;padding-right: 0.75rem;">·</span> Fri Dec 15 00:00:00 EST 2017 <span style="padding-left: 0.75rem;padding-right: 0.75rem;">·</span> Journal of Polymers and the Environment <span style="padding-left: 0.75rem;padding-right: 0.75rem;">·</span> <span class="text-muted" style="padding-right:0.5em;">OSTI ID:</span>1485082 </div> <div class="small" style="line-height:1.4rem;"> <span class="author-link"><a href="/search/author:"Khan, Md. 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