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الحلقي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%DA%A9%D9%84%DB%8C%DA%A9_%D8%AF%DB%8C-%D8%AC%DB%8C%E2%80%8C%D8%A7%D9%85%E2%80%8C%D9%BE%DB%8C" title="سیکلیک دی-جی‌ام‌پی – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیکلیک دی-جی‌ام‌پی" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%DA%A9%D9%84%DB%8C%DA%A9_%D8%AF%DB%8C-%D8%AC%DB%8C%E2%80%8C%D8%A7%D9%85%E2%80%8C%D9%BE%DB%8C" title="سیکلیک دی-جی‌ام‌پی – Persian" lang="fa" hreflang="fa" data-title="سیکلیک دی-جی‌ام‌پی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Di-guanosine_monophosphate_cyclique" title="Di-guanosine monophosphate cyclique – French" lang="fr" hreflang="fr" data-title="Di-guanosine monophosphate cyclique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclisch_diguanylaat" title="Cyclisch diguanylaat – Dutch" lang="nl" hreflang="nl" data-title="Cyclisch diguanylaat" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cyklick%C3%BD_di-GMP" title="Cyklický di-GMP – Slovak" lang="sk" hreflang="sk" data-title="Cyklický di-GMP" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cikli%C4%8Dni_di-GMP" title="Ciklični di-GMP – Serbian" lang="sr" hreflang="sr" data-title="Ciklični di-GMP" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Cikli%C4%8Dni_di-GMP" title="Ciklični di-GMP – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ciklični di-GMP" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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dir="ltr"><p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Cyclic di-GMP </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cyclic-di-GMP.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cyclic-di-GMP.svg/200px-Cyclic-di-GMP.svg.png" decoding="async" width="200" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cyclic-di-GMP.svg/300px-Cyclic-di-GMP.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Cyclic-di-GMP.svg/400px-Cyclic-di-GMP.svg.png 2x" data-file-width="1150" data-file-height="415" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>R</i>,3<i>R</i>,3a<i>S</i>,7a<i>R</i>,9<i>R</i>,10<i>R</i>,10a<i>S</i>,14a<i>R</i>)-2,9-Bis(2-amino-6-oxo-1,6-dihydro-9<i>H</i>-purin-9-yl)-3,5,10,12-tetrahydroxyoctahydro-2<i>H</i>,5<i>H</i>,7<i>H</i>,12<i>H</i>-5λ<sup>5</sup>,12λ<sup>5</sup>-difuro[3,2-<i>d</i>:3′,2′-<i>j</i>][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-5,12-dione</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Cyclic diguanylate; 3',5'-Cyclic diguanylic acid; c-di-GMP; 5GP-5GP</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=61093-23-0">61093-23-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC7%2FN%3DC%28%2FN%29Nc1c7ncn1%5BC%40%40H%5D3O%5BC%40%40H%5D4COP%28%3DO%29%28O%29O%5BC%40H%5D2%5BC%40%40H%5D%28O%29%5BC%40%40H%5D%28O%5BC%40%40H%5D2COP%28%3DO%29%28O%29O%5BC%40H%5D4%5BC%40H%5D3O%29n5c6NC%28%3DN%2FC%28%3DO%29c6nc5%29%5CN">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4883312.html">4883312</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6323195">6323195</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID20976591,">DTXSID801027528 DTXSID20976591, DTXSID801027528</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2649761#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PKFDLKSEZWEFGL-MHARETSRSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PKFDLKSEZWEFGL-MHARETSRBV</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C7/N=C(/N)Nc1c7ncn1[C@@H]3O[C@@H]4COP(=O)(O)O[C@H]2[C@@H](O)[C@@H](O[C@@H]2COP(=O)(O)O[C@H]4[C@H]3O)n5c6NC(=N/C(=O)c6nc5)\N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>20</sub>H<sub>24</sub>N<sub>10</sub>O<sub>14</sub>P<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>690.09 g/mol    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=448724790&page2=Cyclic+di-GMP">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Cyclic di-GMP</b> (also called <b>cyclic diguanylate</b> and <b>c-di-<a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></b>) is a <a href="/wiki/Second_messenger" class="mw-redirect" title="Second messenger">second messenger</a> used in signal transduction in a wide variety of <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>.<sup id="cite_ref-Tamayo_1-0" class="reference"><a href="#cite_note-Tamayo-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Cyclic di-GMP is not known to be used by <a href="/wiki/Archaea" title="Archaea">archaea</a>, and has only been observed in <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a> in <i><a href="/wiki/Dictyostelium" title="Dictyostelium">Dictyostelium</a></i>.<sup id="cite_ref-Chen_2-0" class="reference"><a href="#cite_note-Chen-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The biological role of cyclic di-GMP was first uncovered when it was identified as an allosteric activator of a cellulose synthase found in <i><a href="/wiki/Gluconacetobacter_xylinus" class="mw-redirect" title="Gluconacetobacter xylinus">Gluconacetobacter xylinus</a></i> in order to produce <a href="/wiki/Microbial_cellulose" class="mw-redirect" title="Microbial cellulose">microbial cellulose</a>.<sup id="cite_ref-Ross_1987_3-0" class="reference"><a href="#cite_note-Ross_1987-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>In structure, it is a cycle containing only two <a href="/wiki/Guanine" title="Guanine">guanine</a> bases linked by <a href="/wiki/Ribose" title="Ribose">ribose</a> and <a href="/wiki/Phosphate" title="Phosphate">phosphate</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_di-GMP&action=edit&section=1" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contact with surfaces increases c-di-GMP which increases <a href="/wiki/Gene_transcription" class="mw-redirect" title="Gene transcription">transcription</a>, <a href="/wiki/Gene_translation" class="mw-redirect" title="Gene translation">translation</a>, and <a href="/wiki/Post-translational_modification" title="Post-translational modification">post translation</a> of <a href="/wiki/Exopolysaccharide" class="mw-redirect" title="Exopolysaccharide">exopolysaccharides</a> (EPSs) and other <a href="/wiki/Extracellular_polymeric_substance" title="Extracellular polymeric substance">extracellular polymeric substance</a> matrix components (see the review by Jenal et al 2017).<sup id="cite_ref-Laventie-Jenal-2020_4-0" class="reference"><a href="#cite_note-Laventie-Jenal-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In bacteria, certain signals are communicated by synthesizing or degrading cyclic di-GMP. Cyclic di-GMP is synthesized by <a href="/wiki/Protein" title="Protein">proteins</a> with <a href="/wiki/Diguanylate_cyclase" title="Diguanylate cyclase">diguanylate cyclase</a> activity. These proteins typically have a characteristic <a href="/wiki/GGDEF_domain" title="GGDEF domain">GGDEF</a> motif, which refers to a conserved sequence of five <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>. Degradation of cyclic di-GMP is affected by proteins with <a href="/wiki/Phosphodiesterase" title="Phosphodiesterase">phosphodiesterase</a> activity. These proteins have either an EAL or an HD-GYP amino acid motif. Processes that are known to be regulated by cyclic di-GMP, at least in some organisms, include <a href="/wiki/Biofilm" title="Biofilm">biofilm</a> formation (such as EPS matrices found by Steiner et al 2013),<sup id="cite_ref-Laventie-Jenal-2020_4-1" class="reference"><a href="#cite_note-Laventie-Jenal-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Motility" title="Motility">motility</a> (especially the motile-to-sessile transition, see the review by Jenal et al 2017)<sup id="cite_ref-Laventie-Jenal-2020_4-2" class="reference"><a href="#cite_note-Laventie-Jenal-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Virulence" title="Virulence">virulence</a> factor production. </p> <div class="mw-heading mw-heading2"><h2 id="Regulation">Regulation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_di-GMP&action=edit&section=2" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyclic di-GMP levels are regulated using a variety of mechanisms. Many proteins with GGDEF, <a href="/wiki/EAL_domain" title="EAL domain">EAL</a> or HD-GYP domains are found with other domains that can receive signals, such as <a href="/wiki/PAS_domain" title="PAS domain">PAS domains</a>. Enzymes that degrade or synthesize cyclic di-GMP are believed to be localized to specific regions of the cell, where they influence receivers in a restricted space.<sup id="cite_ref-Tamayo_1-1" class="reference"><a href="#cite_note-Tamayo-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In <i>Gluconacetobacter xylinus,</i> c-di-GMP stimulates the polymerization of glucose into cellulose as a high affinity allosteric activator of the enzyme cellulose synthase.<sup id="cite_ref-Ross_1987_3-1" class="reference"><a href="#cite_note-Ross_1987-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Some diguanylate cyclase enzymes are allosterically inhibited by cyclic di-GMP. </p><p>Cyclic di-GMP levels regulate other processes via a number of mechanisms. The <i>Gluconacetobacter xylinus</i> cellulose synthase is allosterically stimulated by cyclic di-GMP, presenting a mechanism by which cyclic di-GMP can regulate cellulose synthase activity. The PilZ domain has been shown to bind cyclic di-GMP and is believed to be involved in cyclic di-GMP-dependent regulation, but the mechanism by which it does this is unknown. Recent structural studies of PilZ domains from two bacterial species have demonstrated that PilZ domains change conformation drastically upon binding to cyclic di-GMP.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This leads to the strong inference that conformational changes in PilZ domains allow the activity of targeted effector proteins (such as cellulose synthase) to be regulated by cyclic di-GMP. <a href="/wiki/Riboswitch" title="Riboswitch">Riboswitches</a> called the <a href="/wiki/Cyclic_di-GMP-I_riboswitch" title="Cyclic di-GMP-I riboswitch">cyclic di-GMP-I riboswitch</a> and <a href="/wiki/Cyclic_di-GMP-II_riboswitch" title="Cyclic di-GMP-II riboswitch">cyclic di-GMP-II riboswitch</a> regulate gene expression in response to cyclic di-GMP concentrations in a variety of bacteria, but not all bacteria that are known to use cyclic di-GMP. </p> <div class="mw-heading mw-heading2"><h2 id="Host-association">Host-association</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_di-GMP&action=edit&section=3" title="Edit section: Host-association"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyclic di-GMP has been linked to host-association in multiple <i>Pseudomonas</i> species. In an experiment where <i>Pseudomonas lurida</i> was grown in association with the nematode host <i>Caenorhabditis elegans</i> genetic mutations were observed in certain genes that upregulated c-di-GMP, causing a host specialist morphotype to emerge. The mutations affecting c-di-GMP regulation were uncovered with whole genome sequencing. Genes <i>wspE</i> and <i>wspF</i> from the wsp operon exhibited mutations that upregulated c-di-GMP. Additionally, mutations in the gene <i>rph</i> were determined to also affect c-di-GMP expression, which is a novel discovery because <i>rph</i> has not previously been linked to c-di-GMP regulation.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>For a review of c-di-GMP roles in <i><a href="/wiki/Caulobacter_crescentus" title="Caulobacter crescentus">Caulobacter crescentus</a></i>, <i><a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i>, <i><a href="/wiki/Komagataeibacter_xylinus" title="Komagataeibacter xylinus">Komagataeibacter xylinus</a></i>/<i>Gluconacetobacter xylinus</i>, <i><a href="/wiki/Myxococcus_xanthus" title="Myxococcus xanthus">Myxococcus xanthus</a></i>, <i><a href="/wiki/Bdellovibrio_bacteriovorus" class="mw-redirect" title="Bdellovibrio bacteriovorus">Bdellovibrio bacteriovorus</a></i> and <i><a href="/wiki/Pseudomonas_fluorescens" title="Pseudomonas fluorescens">Pseudomonas fluorescens</a></i> see Jenal et al 2017.<sup id="cite_ref-Laventie-Jenal-2020_4-3" class="reference"><a href="#cite_note-Laventie-Jenal-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_di-GMP&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Cyclic_di-AMP" title="Cyclic di-AMP">Cyclic di-AMP</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclic_di-GMP&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Tamayo-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Tamayo_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Tamayo_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription 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style="font-size:114%;margin:0 4em"><a href="/wiki/Nucleic_acid" title="Nucleic acid">Nucleic acid</a> constituents</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">Nucleobase</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Purine" title="Purine">Purine</a> <ul><li><a href="/wiki/Adenine" title="Adenine">Adenine</a></li> <li><a href="/wiki/Guanine" title="Guanine">Guanine</a></li> <li><a href="/wiki/Hypoxanthine" title="Hypoxanthine">Hypoxanthine</a></li> <li><a href="/wiki/Xanthine" title="Xanthine">Xanthine</a></li> <li><a href="/wiki/Purine_analogue" title="Purine analogue">Purine analogue</a></li></ul></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a> <ul><li><a href="/wiki/Uracil" title="Uracil">Uracil</a></li> <li><a href="/wiki/Thymine" title="Thymine">Thymine</a></li> <li><a href="/wiki/Cytosine" title="Cytosine">Cytosine</a></li> <li><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine analogue</a></li></ul></li> <li><a href="/wiki/Base_pair#Unnatural_base_pair_(UBP)" title="Base pair">Unnatural base pair (UBP)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleoside" title="Nucleoside">Nucleoside</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ribonucleoside" title="Ribonucleoside">Ribonucleoside</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Guanosine" title="Guanosine">Guanosine</a></li> <li><a href="/wiki/5-Methyluridine" title="5-Methyluridine">5-Methyluridine</a></li> <li><a href="/wiki/Uridine" title="Uridine">Uridine</a></li> <li><a href="/wiki/5-Methylcytidine" title="5-Methylcytidine">5-Methylcytidine</a></li> <li><a href="/wiki/Cytidine" title="Cytidine">Cytidine</a></li> <li><a href="/wiki/Pseudouridine" title="Pseudouridine">Pseudouridine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/N6-Methyladenosine" title="N6-Methyladenosine"><i>N</i><sup>6</sup>-Methyladenosine</a></li> <li><a href="/wiki/Xanthosine" title="Xanthosine">Xanthosine</a></li> <li><a href="/wiki/Wybutosine" title="Wybutosine">Wybutosine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleoside" class="mw-redirect" title="Deoxyribonucleoside">Deoxyribonucleoside</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine" title="Deoxyadenosine">Deoxyadenosine</a></li> <li><a href="/wiki/Deoxyguanosine" title="Deoxyguanosine">Deoxyguanosine</a></li> <li><a href="/wiki/Thymidine" title="Thymidine">Thymidine</a></li> <li><a href="/wiki/Deoxyuridine" title="Deoxyuridine">Deoxyuridine</a></li> <li><a href="/wiki/Deoxycytidine" title="Deoxycytidine">Deoxycytidine</a></li> <li><a href="/w/index.php?title=Deoxyinosine&action=edit&redlink=1" class="new" title="Deoxyinosine (page does not exist)">Deoxyinosine</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine&action=edit&redlink=1" class="new" title="Deoxyxanthosine (page does not exist)">Deoxyxanthosine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleotide" title="Nucleotide">Nucleotide</a><br />(Nucleoside monophosphate)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ribonucleotide" title="Ribonucleotide">Ribonucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">AMP</a></li> <li><a href="/wiki/Guanosine_monophosphate" title="Guanosine monophosphate">GMP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_monophosphate&action=edit&redlink=1" class="new" title="5-Methyluridine monophosphate (page does not exist)">m<sup>5</sup>UMP</a></li> <li><a href="/wiki/Uridine_monophosphate" title="Uridine monophosphate">UMP</a></li> <li><a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">CMP</a></li> <li><a href="/wiki/Inosinic_acid" title="Inosinic acid">IMP</a></li> <li><a href="/wiki/Xanthosine_monophosphate" title="Xanthosine monophosphate">XMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_monophosphate" title="Deoxyadenosine monophosphate">dAMP</a></li> <li><a href="/wiki/Deoxyguanosine_monophosphate" title="Deoxyguanosine monophosphate">dGMP</a></li> <li><a href="/wiki/Thymidine_monophosphate" title="Thymidine monophosphate">dTMP</a></li> <li><a href="/wiki/Deoxyuridine_monophosphate" title="Deoxyuridine monophosphate">dUMP</a></li> <li><a href="/wiki/Deoxycytidine_monophosphate" title="Deoxycytidine monophosphate">dCMP</a></li> <li><a href="/wiki/Deoxyinosine_monophosphate" title="Deoxyinosine monophosphate">dIMP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_monophosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine monophosphate (page does not exist)">dXMP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyclic_nucleotide" title="Cyclic nucleotide">Cyclic nucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclic_adenosine_monophosphate" title="Cyclic adenosine monophosphate">cAMP</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate" title="Cyclic guanosine monophosphate">cGMP</a></li> <li><a class="mw-selflink selflink">c-di-GMP</a></li> <li><a href="/wiki/Cyclic_di-AMP" title="Cyclic di-AMP">c-di-AMP</a></li> <li><a href="/wiki/Cyclic_ADP-ribose" title="Cyclic ADP-ribose">cADPR</a></li> <li><a href="/wiki/Cyclic_guanosine_monophosphate%E2%80%93adenosine_monophosphate" title="Cyclic guanosine monophosphate–adenosine monophosphate">cGAMP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nucleoside diphosphate</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a></li> <li><a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a></li> <li><a href="/w/index.php?title=5-Methyluridine_diphosphate&action=edit&redlink=1" class="new" title="5-Methyluridine diphosphate (page does not exist)">m<sup>5</sup>UDP</a></li> <li><a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a></li> <li><a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a></li> <li><a href="/w/index.php?title=Xanthosine_diphosphate&action=edit&redlink=1" class="new" title="Xanthosine diphosphate (page does not exist)">Xanthosine diphosphate</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_diphosphate" title="Deoxyadenosine diphosphate">dADP</a></li> <li><a href="/wiki/Deoxyguanosine_diphosphate" title="Deoxyguanosine diphosphate">dGDP</a></li> <li><a href="/wiki/Thymidine_diphosphate" title="Thymidine diphosphate">dTDP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_diphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine diphosphate (page does not exist)">dUDP</a></li> <li><a href="/wiki/Deoxycytidine_diphosphate" title="Deoxycytidine diphosphate">dCDP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleoside_triphosphate" title="Nucleoside triphosphate">Nucleoside triphosphate</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a></li> <li><a href="/wiki/5-Methyluridine_triphosphate" title="5-Methyluridine triphosphate">m<sup>5</sup>UTP</a></li> <li><a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a></li> <li><a href="/wiki/Xanthosine_triphosphate" title="Xanthosine triphosphate">XTP</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxyadenosine_triphosphate" title="Deoxyadenosine triphosphate">dATP</a></li> <li><a href="/wiki/Deoxyguanosine_triphosphate" title="Deoxyguanosine triphosphate">dGTP</a></li> <li><a href="/wiki/Thymidine_triphosphate" title="Thymidine triphosphate">dTTP</a></li> <li><a href="/w/index.php?title=Deoxyuridine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyuridine triphosphate (page does not exist)">dUTP</a></li> <li><a href="/wiki/Deoxycytidine_triphosphate" title="Deoxycytidine triphosphate">dCTP</a></li> <li><a href="/w/index.php?title=Deoxyinosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyinosine triphosphate (page does not exist)">dITP</a></li> <li><a href="/w/index.php?title=Deoxyxanthosine_triphosphate&action=edit&redlink=1" class="new" title="Deoxyxanthosine triphosphate (page does not exist)">dXTP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Cyclic_di-GMP&oldid=1211568438">https://en.wikipedia.org/w/index.php?title=Cyclic_di-GMP&oldid=1211568438</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Nucleotides" title="Category:Nucleotides">Nucleotides</a></li><li><a href="/wiki/Category:Cyclic_nucleotides" 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