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<h1 id="firstHeading" class="firstHeading mw-first-heading">Ap4A</h1>
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<div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div>
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<table class="infobox ib-chembox">
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<caption>Ap4A
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<td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Diadenosine_tetraphosphate.svg" class="image"><img alt="Diadenosine tetraphosphate.svg" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Diadenosine_tetraphosphate.svg/250px-Diadenosine_tetraphosphate.svg.png" decoding="async" width="250" height="43" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Diadenosine_tetraphosphate.svg/375px-Diadenosine_tetraphosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Diadenosine_tetraphosphate.svg/500px-Diadenosine_tetraphosphate.svg.png 2x" data-file-width="1735" data-file-height="295" /></a>
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</td></tr>
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<tr>
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<th colspan="2" style="background: #f8eaba; text-align: center;">Names
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<td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a>
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<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display:inline-block; line-height:1.2em; padding:0.1em 0;max-width:22em;"><i>O</i><sup>1</sup>,<i>O</i><sup>7</sup>-Bis{[(2<i>R</i>,3<i>S</i>,4<i>R</i>,5<i>R</i>)-5-(6-amino-9<i>H</i>-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen tetraphosphate</div></div>
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</td></tr>
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<td colspan="2" style="text-align:left;">Other names
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<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Diadenosine tetraphosphate; 5',5'''-Diadenosine tetraphosphate; AppppA</div>
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<th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers
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</th></tr>
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<tr>
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<td><div style="display:inline-block; line-height:1.2em; padding:0.1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>
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</td>
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<td><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5542-28-9">5542-28-9</a></span></li></ul></div>
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</td></tr>
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<td><div style="display:inline-block; line-height:1.2em; padding:0.1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div>
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</td>
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<td><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=C1%3DNC2%3DC%28C%28%3DN1%29N%29N%3DCN2%5BC%40H%5D3%5BC%40%40H%5D%28%5BC%40%40H%5D%28%5BC%40H%5D%28O3%29COP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OP%28%3DO%29%28O%29OC%5BC%40%40H%5D4%5BC%40H%5D%28%5BC%40H%5D%28%5BC%40%40H%5D%28O4%29N5C%3DNC6%3DC5N%3DCN%3DC6N%29O%29O%29O%29O">Interactive image</a></span></li></ul></div>
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</td></tr>
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<tr>
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<td><div style="display:inline-block; line-height:1.2em; padding:0.1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>
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</td>
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<td><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/21706">21706</a></span></li></ul></div>
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<td colspan="2"><div class="mw-collapsible mw-collapsed" style="text-align: center; font-size: 95%;">
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<div style="line-height: 1.6em; font-weight: bold; font-size: 100%; text-align: left; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" title="Simplified molecular-input line-entry system">SMILES</a></div></div>
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<ul class="mw-collapsible-content" style="font-size: 105%; margin-top: 0; margin-bottom: 0; line-height: inherit; text-align: left; list-style: none 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%;">C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C5N=CN=C6N)O)O)O)O</div></li></ul>
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</div>
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</td></tr>
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<tr>
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<th colspan="2" style="background: #f8eaba; text-align: center;">Properties
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</th></tr>
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<tr>
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<td><div style="display:inline-block; line-height:1.2em; padding:0.1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div>
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</td>
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<td><span title="Carbon">C</span><sub>20</sub><span title="Hydrogen">H</span><sub>28</sub><span title="Nitrogen">N</span><sub>10</sub><span title="Oxygen">O</span><sub>19</sub><span title="Phosphorus">P</span><sub>4</sub>
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</td></tr>
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<tr>
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<td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a>
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</td>
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<td><span class="nowrap"><span data-sort-value="7002836390000000000♠"></span>836.390</span> g·mol<sup>−1</sup>  
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<td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display:inline-block; line-height:1.2em; padding:0.1em 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>
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<div style="margin-top: 0.3em;"></div>
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<div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div>
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</td></tr>
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</tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div>
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<p><b>Diadenosine tetraphosphate</b> or <b>Ap4A</b> is a putative <a href="/wiki/Alarmone" title="Alarmone">alarmone</a>, ubiquitous in nature being common to everything from <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> to <a href="/wiki/Human" title="Human">humans</a>. It is made up of two adenosines joined together by a 5′-5′ linked chain of four phosphates. Adenosine polyphosphates are capable of inducing multiple <a href="/wiki/Physiological" class="mw-redirect" title="Physiological">physiological</a> effects.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1">[1]</a></sup>
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</p>
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<div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none" /><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div>
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<ul>
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<li class="toclevel-1 tocsection-1"><a href="#Function"><span class="tocnumber">1</span> <span class="toctext">Function</span></a>
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<ul>
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<li class="toclevel-2 tocsection-2"><a href="#In_Eukaryotes"><span class="tocnumber">1.1</span> <span class="toctext">In Eukaryotes</span></a></li>
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<li class="toclevel-2 tocsection-3"><a href="#In_Prokaryotes"><span class="tocnumber">1.2</span> <span class="toctext">In Prokaryotes</span></a></li>
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</ul>
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</li>
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<li class="toclevel-1 tocsection-4"><a href="#References"><span class="tocnumber">2</span> <span class="toctext">References</span></a></li>
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<h2><span class="mw-headline" id="Function">Function</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ap4A&action=edit&section=1" title="Edit section: Function">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
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<h3><span class="mw-headline" id="In_Eukaryotes">In Eukaryotes</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ap4A&action=edit&section=2" title="Edit section: In Eukaryotes">edit</a><span class="mw-editsection-bracket">]</span></span></h3>
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<p>Ap4A can be created by a non-canonical activity of the Lysyl-<a href="/wiki/Aminoacyl_tRNA_synthetase" title="Aminoacyl tRNA synthetase">tRNA synthetase</a> (LysRS). This function of LysRS is activated by the phosphorylation of LysRS on serine 207, its subsequent dissociation from the multi-synthetase complex (MSC).<sup id="cite_ref-2" class="reference"><a href="#cite_note-2">[2]</a></sup> The molecule's role as a second messenger has recently been discovered in The <a href="/wiki/KARS_(gene)" title="KARS (gene)">LysRS</a>-Ap4A-<a href="/wiki/MITF" class="mw-redirect" title="MITF">MITF</a> signaling pathway.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3">[3]</a></sup> Ap4A binds to the MITF-HINT1 inhibitory complex, specifically to the molecule <a href="/wiki/HINT1" title="HINT1">histidine triad nucleotide–binding protein 1</a>(HINT1), releasing the Microphthalmia-associated transcription factor (MITF) and causing an increase in the transcription of its target genes.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4">[4]</a></sup> Ap4A also positively regulates the activity of the transcription factor <a href="/wiki/USF2" title="USF2">USF2</a> through a similar molecular mechanism to that of MITF.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5">[5]</a></sup>
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</p><p>It has also been shown, that Ap4A plays a role in the functionality of <a href="/wiki/Dendritic_cell" title="Dendritic cell">dendritic cells</a> (DCs). An increase in the intracellular amount Improves their motility and antigen presenting ability through alterations in small <a href="/wiki/GTPase" title="GTPase">GTPases</a> present in the cells. This was discovered by creating mice deficient in the enzyme <i>NUDT2,</i> which serves as an Ap4A <a href="/wiki/Hydrolase" title="Hydrolase">hydrolase</a> and thus controls the levels of Ap4A in the cell.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6">[6]</a></sup> Ap4A, however, has also been shown to cause <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> in several cell lines through an unknown mechanism, the degradation of Ap4A was necessary for the process as hydrolysis‐resistant analogues of the molecule showed no apoptotic activity.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7">[7]</a></sup>
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</p>
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<h3><span class="mw-headline" id="In_Prokaryotes">In Prokaryotes</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ap4A&action=edit&section=3" title="Edit section: In Prokaryotes">edit</a><span class="mw-editsection-bracket">]</span></span></h3>
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<p>In E. Coli, Ap4A has been shown to function as an alarmone, as the intracellular concentrantion of the molecule increases upon heat stress.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8">[8]</a></sup> Ap4A can also be incorporated into RNA as a <a href="/wiki/Five-prime_cap" title="Five-prime cap">5' Cap</a> along with other dinucleoside polyphosphates. It serves as a substrate for the <a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a> and the intracellular levels of these capped RNAs increase upon stress, suggesting that the cap adds a level of stability to the <a href="/wiki/RNA" title="RNA">RNA</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9">[9]</a></sup>
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</p><p><i><a href="/wiki/Myxococcus_xanthus" title="Myxococcus xanthus">Myxococcus xanthus</a></i> is a type of <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">Gram-negative bacteria</a>, and <i>M. xanthus</i> lysyl-tRNA synthetase (LysS) is an enzyme from the bacteria that synthesizes diadenosine tetraphosphates (Ap4A) when <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP) is present. Diadenosine pentaphosphate (Ap5A) is synthesized from Ap4A with ATP.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10">[10]</a></sup>
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</p>
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<h2><span class="mw-headline" id="References">References</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ap4A&action=edit&section=4" title="Edit section: References">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
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<li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1067248974"/><cite id="CITEREFDespotovićBrandisSavidorLevin2017" class="citation journal cs1">Despotović, Dragana; Brandis, Alexander; Savidor, Alon; Levin, Yishai; Fumagalli, Laura; Tawfik, Dan S. (2017). <a rel="nofollow" class="external text" href="https://febs.onlinelibrary.wiley.com/doi/abs/10.1111/febs.14113">"Diadenosine tetraphosphate (Ap4A) – an E. coli alarmone or a damage metabolite?"</a>. <i>The FEBS Journal</i>. <b>284</b> (14): 2194–2215. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="cs1-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Ffebs.14113">10.1111/febs.14113</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="//www.worldcat.org/issn/1742-4658">1742-4658</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/28516732">28516732</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+FEBS+Journal&rft.atitle=Diadenosine+tetraphosphate+%28Ap4A%29+%E2%80%93+an+E.+coli+alarmone+or+a+damage+metabolite%3F&rft.volume=284&rft.issue=14&rft.pages=2194-2215&rft.date=2017&rft.issn=1742-4658&rft_id=info%3Apmid%2F28516732&rft_id=info%3Adoi%2F10.1111%2Ffebs.14113&rft.aulast=Despotovi%C4%87&rft.aufirst=Dragana&rft.au=Brandis%2C+Alexander&rft.au=Savidor%2C+Alon&rft.au=Levin%2C+Yishai&rft.au=Fumagalli%2C+Laura&rft.au=Tawfik%2C+Dan+S.&rft_id=https%3A%2F%2Ffebs.onlinelibrary.wiley.com%2Fdoi%2Fabs%2F10.1111%2Ffebs.14113&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAp4A" class="Z3988"></span></span>
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<li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1067248974"/><cite id="CITEREFHudečekBenoniReyes-GutierrezCulka2020" class="citation journal cs1">Hudeček, Oldřich; Benoni, Roberto; Reyes-Gutierrez, Paul E.; Culka, Martin; Šanderová, Hana; Hubálek, Martin; Rulíšek, Lubomír; Cvačka, Josef; Krásný, Libor; Cahová, Hana (2020-02-26). <a rel="nofollow" class="external text" href="https://www.nature.com/articles/s41467-020-14896-8">"Dinucleoside polyphosphates act as 5′-RNA caps in bacteria"</a>. <i>Nature Communications</i>. <b>11</b> (1): 1052. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2020NatCo..11.1052H">2020NatCo..11.1052H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="cs1-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41467-020-14896-8">10.1038/s41467-020-14896-8</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="//www.worldcat.org/issn/2041-1723">2041-1723</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="cs1-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pmc/articles/PMC7044304">7044304</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/32103016">32103016</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Communications&rft.atitle=Dinucleoside+polyphosphates+act+as+5%E2%80%B2-RNA+caps+in+bacteria&rft.volume=11&rft.issue=1&rft.pages=1052&rft.date=2020-02-26&rft_id=%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7044304%23id-name%3DPMC&rft_id=info%3Abibcode%2F2020NatCo..11.1052H&rft_id=info%3Apmid%2F32103016&rft_id=info%3Adoi%2F10.1038%2Fs41467-020-14896-8&rft.issn=2041-1723&rft.aulast=Hude%C4%8Dek&rft.aufirst=Old%C5%99ich&rft.au=Benoni%2C+Roberto&rft.au=Reyes-Gutierrez%2C+Paul+E.&rft.au=Culka%2C+Martin&rft.au=%C5%A0anderov%C3%A1%2C+Hana&rft.au=Hub%C3%A1lek%2C+Martin&rft.au=Rul%C3%AD%C5%A1ek%2C+Lubom%C3%ADr&rft.au=Cva%C4%8Dka%2C+Josef&rft.au=Kr%C3%A1sn%C3%BD%2C+Libor&rft.au=Cahov%C3%A1%2C+Hana&rft_id=https%3A%2F%2Fwww.nature.com%2Farticles%2Fs41467-020-14896-8&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAp4A" class="Z3988"></span></span>
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<li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1067248974"/><cite id="CITEREFKimuraTanakaOka2018" class="citation journal cs1">Kimura, Yoshio; Tanaka, Chihiro; Oka, Manami (July 2018). "Identification of Major Enzymes Involved in the Synthesis of Diadenosine Tetraphosphate and/or Adenosine Tetraphosphate in Myxococcus xanthus". <i>Current Microbiology</i>. <b>75</b> (7): 811–817. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00284-018-1452-x">10.1007/s00284-018-1452-x</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="//www.worldcat.org/issn/1432-0991">1432-0991</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/29468302">29468302</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:3402370">3402370</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Microbiology&rft.atitle=Identification+of+Major+Enzymes+Involved+in+the+Synthesis+of+Diadenosine+Tetraphosphate+and%2For+Adenosine+Tetraphosphate+in+Myxococcus+xanthus&rft.volume=75&rft.issue=7&rft.pages=811-817&rft.date=2018-07&rft.issn=1432-0991&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A3402370%23id-name%3DS2CID&rft_id=info%3Apmid%2F29468302&rft_id=info%3Adoi%2F10.1007%2Fs00284-018-1452-x&rft.aulast=Kimura&rft.aufirst=Yoshio&rft.au=Tanaka%2C+Chihiro&rft.au=Oka%2C+Manami&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAp4A" class="Z3988"></span></span>
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