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<title>Tetrapeptide</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Tetrapeptide</span></span>

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<p>A <b>tetrapeptide</b> is a <a href="Peptide" title="Peptide">peptide</a>, classified as an <a href="Oligopeptide" title="Oligopeptide">oligopeptide</a>, since it only consists of four <a href="Amino_acids" class="mw-redirect" title="Amino acids">amino acids</a> joined by <a href="Peptide_bond" title="Peptide bond">peptide bonds</a>. Many tetrapeptides are <a href="Pharmacology" title="Pharmacology">pharmacologically</a> active, often showing affinity and specificity for a variety of receptors in protein-protein signaling. Present in nature are both linear and <b>cyclic tetrapeptides</b> (CTPs), the latter of which mimics protein reverse turns which are often present on the surface of proteins and druggable targets.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Tetrapeptides may be <a href="Cyclic_compound" title="Cyclic compound">cyclized</a> by a fourth peptide bond or other <a href="Covalent_bonds" class="mw-redirect" title="Covalent bonds">covalent bonds</a>.

</p><p>Examples of tetrapeptides are:

</p>

<ul><li><a href="Tuftsin" title="Tuftsin">Tuftsin</a> (<small>L</small>-threonyl-<small>L</small>-lysyl-<small>L</small>-prolyl-<small>L</small>-arginine) is a peptide related primarily to the <a href="Immune_system" title="Immune system">immune system</a> function.</li>

<li>Rigin (glycyl-<small>L</small>-glutaminyl-<small>L</small>-prolyl-<small>L</small>-arginine) is a tetrapeptide with functions similar to those of tuftsin.</li>

<li>Postin (Lys-Pro-Pro-Arg) is the N-terminal tetrapeptide of <a href="Cystatin_C" title="Cystatin C">cystatin C</a> and an antagonist of tuftsin.</li>

<li><a href="Endomorphin" title="Endomorphin">Endomorphin-1</a> (H-Tyr-Pro-Trp-Phe-NH<sub>2</sub>) and <a href="Endomorphin" title="Endomorphin">endomorphin-2</a> (H-Tyr-Pro-Phe-Phe-NH<sub>2</sub>) are peptide amides with the highest known affinity and specificity for the <a href="Mu_opioid_receptor" class="mw-redirect" title="Mu opioid receptor">μ opioid receptor</a>.</li>

<li><a href="Morphiceptin" title="Morphiceptin">Morphiceptin</a> (H-Tyr-Pro-Phe-Pro-NH<sub>2</sub>) is a <a href="Casomorphin" title="Casomorphin">casomorphin</a> peptide isolated from β-<a href="Casein" title="Casein">casein</a>.</li>

<li><a href="Gluten_exorphine" class="mw-redirect" title="Gluten exorphine">Gluten exorphines</a> A4 (H-Gly-Tyr-Tyr-Pro-OH) and B4 (H-Tyr-Gly-Gly-Trp-OH) are peptides isolated from <a href="Gluten" title="Gluten">gluten</a>.</li>

<li>Tyrosine-MIF-1 (H-Tyr-Pro-Leu-Gly-NH<sub>2</sub>) is an endogenous opioid modulator.</li>

<li><a href="Tetragastrin" class="mw-redirect" title="Tetragastrin">Tetragastrin</a> (<i>N</i>-((phenylmethoxy)carbonyl)-<small>L</small>-tryptophyl-<small>L</small>-methionyl-<small>L</small>-aspartyl-<small>L</small>-phenylalaninamide) is the C-terminal tetrapeptide of <a href="Gastrin" title="Gastrin">gastrin</a>. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin.</li>

<li>Kentsin (H-Thr-Pro-Arg-Lys-OH) is a contraceptive peptide first isolated from female <a href="Hamster" title="Hamster">hamsters</a>.</li>

<li>Achatin-I (glycyl-phenylalanyl-alanyl-aspartic acid) is a neuroexcitatory tetrapeptide from <a href="Achatina_fulica" class="mw-redirect" title="Achatina fulica">giant African snail</a> (<i>Achatina fulica</i>).</li>

<li><a href="Tentoxin" title="Tentoxin">Tentoxin</a> (cyclo(<i>N</i>-methyl-<small>L</small>-alanyl-<small>L</small>-leucyl-<i>N</i>-methyl-<i>trans</i>-dehydrophenyl-alanyl-glycyl)) is a natural cyclic tetrapeptide produced by phytopathogenic fungi from genus <i><a href="Alternaria" title="Alternaria">Alternaria</a></i>.</li>

<li><a href="Rapastinel" title="Rapastinel">Rapastinel</a> (H-Thr-Pro-Pro-Thr-NH<sub>2</sub>) is a <a href="Partial_agonist" title="Partial agonist">partial agonist</a> of the <a href="NMDA_receptor" title="NMDA receptor">NMDA receptor</a>.</li>

<li><a href="Nonribosomal_peptide" title="Nonribosomal peptide">HC-toxin</a>, cyclo(D-Pro-L-Ala-D-Ala-L-Aeo), where Aeo is 2-amino-8-oxo-9,10-epoxy decanoic acid, is a virulence factor for the fungus <i><a href="Cochliobolus_carbonum" title="Cochliobolus carbonum">Cochliobolus carbonum</a></i> on its host, <a href="Maize" title="Maize">maize</a>.</li>

<li><a href="Elamipretide" title="Elamipretide">Elamipretide</a>, (D-Arg-dimethylTyr-Lys-Phe-NH2) a drug candidate that targets <a href="Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul>

<div class="mw-heading mw-heading2"><h2 id="Cyclic_Tetrapeptides">Cyclic Tetrapeptides</h2></div>

<p>Cyclic tetrapeptides are a class of drugs that contain an α-epoxyketone group that has the potential to alkylate the HDAC active site.<sup id="cite_ref-Chakravarty_2021_5-0" class="reference"><a href="#cite_note-Chakravarty_2021-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The HDAC active site, also known as histone deacetylase, are isozymes that modulate numerous regulatory signals and pathways within biological systems. They serve as targets for drug design.<sup id="cite_ref-pmid31606087_6-0" class="reference"><a href="#cite_note-pmid31606087-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> If the cyclic tetrapeptides were to alkylate the HDAC active site, they would deactivate the HDAC catalytic pocket. The tetra-peptide tuftsin (Thr–Lys–Pro–Arg), has been reported to affect a wide variety of biological responses in neutrophils and mononuclear phagocytes and also phagocytosis. It has also been reported that a tetra-peptide with the amino acid sequence, RGDS, that is from the cell-binding domain of the fibronectin molecule, is capable of blocking fibronectin from attaching to the cells. Based on that report, they were able to suggest that the RGDS tetra-peptide is capable of blocking RPE attachment to a variety of extracellular matrix component including; fibronectin, type I collagen, type II collagen, laminin, and lens capsule basement membrane. By utilizing time-lapse cinematography, it has been shown that the RGDS tetra-peptide inhibits the ability of cells to contract collagen.<sup id="cite_ref-Chakravarty_2021_5-1" class="reference"><a href="#cite_note-Chakravarty_2021-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Some_examples_of_how_tetrapeptides_are_utilized_in_scientific_research">Some examples of how tetrapeptides are utilized in scientific research</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Tentoxin">Tentoxin</h3></div>

<p>Tentoxin is most commonly known as a naturally occurring phytotoxic cyclic tetra-peptide that is excreted by fungi of the <i>Alternaria alternata</i> family. There were four total syntheses of tentoxin that were published to this day that gave very poor total yields. These poor yields were mainly due to the introduction of the dehydro amino acid, more specifically the cyclization step. There was a method developed in order to stereospecifically introduce Z-dehydrophenylalanine by a modified Erlenmeyer adolization reaction.<sup id="cite_ref-Loiseau_2002_7-0" class="reference"><a href="#cite_note-Loiseau_2002-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> An aldol reaction is a transformation that is due to the dimerization of an aldehyde (or ketone) to a beta-hydroxy aldehyde (or ketone) by alpha C-H addition of one reactant molecule to the carbonyl group of a second reactant molecule. This reaction requires at least one of the reactants to have hydrogens.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The precursor of tentoxin, the linear tetrapeptide (Boc-R1Ala-Leu-R2ΔZPhe-Gly-OMe), was obtained from Boc-Leu-Gly-OH with a 72% yield. This linear tetrapeptide with carbon-14 was utilized to study the four cyclization reagents, DPPA, DCC-PfpOH, HBTU, and HATU. By doing so, this gave the tentoxin an 81% cyclization yield.<sup id="cite_ref-Loiseau_2002_7-1" class="reference"><a href="#cite_note-Loiseau_2002-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Tetra-peptide_Inhibitor">Tetra-peptide Inhibitor</h3></div>

<p>In order to understand more about the mechanisms that are utilized to regulate the activation of caspases, a study was conducted to identify the conditions that would potentially lead to as complete and synchronous an induction of apoptosis as possible using a tetrapeptide inhibitor. This was achieved by utilizing HL-60 cells, which are a human promyelocytic cell line, in order to show that both anisomycin and geranylgeraniol are able to induce apoptosis in approximately 80% of the cells within two hours.<sup id="cite_ref-Polverino_1997_9-0" class="reference"><a href="#cite_note-Polverino_1997-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Anisomycin is a translational inhibitor that is secreted by Streptomyces spp., it strongly activates the stress-activated mitogen-activate protein kinases, JNK/SAPK and p38/RK in mammalian cells. This results in the rapid induction of immediate-early genes within the nuclease.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Geranylgeraniol is a diterpene alcohol that is used for perfume ingredients and as a raw material for synthesizing vitamins such as; vitamin A and E. It is also reported to prevent inhibition of the osteoclast formation as well as bone resorption in vitro. It has also show to induce anticancer, antitumor, and antileishmanial potentials.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>

</p><p>The induction of apoptosis in the HL-60 cells is accompanied by the processing of activation of caspase-3 and potentially caspase-2. Benzyloxycarbonyl-Val-Ala-Asp-(OMe)-fluoromethylketone (zVAD.fmk), a tetrapeptide inhibitor of caspases, was added to prolong the induction of apoptosis that was induced by either agent. It also enabled some cells to continue to grow up to 72 hours after the treatment. This method was essential to the study to better understand the mechanisms of apoptosis.<sup id="cite_ref-Polverino_1997_9-1" class="reference"><a href="#cite_note-Polverino_1997-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Novel_Vaccine_Adjuvant">Novel Vaccine Adjuvant</h3></div>

<p>A novel vaccine adjuvant that's purpose is to evoke both humoral and cellular immune responses was reported. This vaccine adjuvant was found from a supramolecular hydrogel of a self-assembling D-tetra-peptide. Prior pioneering work has found that self-assembling peptides can serve as self-adjuvated vaccines through the covalent conjugation of peptide or protein antigens, but that cannot elicit strong CD8^+ T-cell responses.<sup id="cite_ref-Luo_2017_12-0" class="reference"><a href="#cite_note-Luo_2017-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> However, in a recent study it has been found that the self-assembling L-peptide derivative (Nap-GFFY-NMe, naphthylacetic acid modified tetra-peptide of GFFY with C-terminal methyl amide group) that was formed fromm the phosphatase, could co-assemble with HIV DNA molecules and raise both humoral and cellular immune responses against HIV. It has been reported that the large-scale synthesis of the phosphorylated precursor (Nap-GFFpY-NMe or Nap-GFFpY-OMe (naphthylacetic acid modified phosphorylated tetra-peptide of GFFpY with C-terminal methyl ester group)) is extremely difficult. It has also been reported that the need of enzyme triggering could possibly cause side effects including; reproducibility problems and composition variation.<sup id="cite_ref-Luo_2017_12-1" class="reference"><a href="#cite_note-Luo_2017-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> If they are able to develop a peptide hydrogel as a vaccine adjuvant that contains a well-defined molecular structure and a very simple formulation mode, it would be very promising.

</p>

<div class="mw-heading mw-heading3"><h3 id="Trapoxin">Trapoxin</h3></div>

<p>Trapoxin, (cyclo-(L-phenylalanyl-L-phenylalanyl-D-pipecolinyl-L-2-amino-8- oxo-9,10-epoxy-decanoyl)), is commonly known as an anti-tumor cyclic tetra-peptide. In a prior study, it has been found that the fungal product, Trapoxin, can induce morphological reversion from transformed to normal in sis-transformed NIH3T3 fibroblasts. It was also found that trapoxin can cause highly acetylated core histones in many different mammalian cell lines to accumulate. Vitro experiments were conducted, and it was found that a low concentration of trapoxin could irreversibly inhibit deacetylation of acetylated histone molecules. The study reported that this could be due to the chemical reduction of an epoxide group, that is in trapoxin, completely abolishing the inhibitory activity. This suggested that trapoxin binds covalently to the histone deacetylase via the epoxide. On the contrary, the inhibition by trichostatin A, which is a known potent inhibitor of histone deacetylase, could be reversible. Despite their mode of inhibitions being different, trapoxin and trichostatin A had nearly the same biological effects on the cell cycle. The in vivo effects that are commonly induced by these agents could be attributed to histone hyperacetylation that results from the inhibition of histone deacetylase, which was strongly suggested from the results.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li><a href="Dipeptide" title="Dipeptide">Dipeptide</a></li>

<li><a href="Tripeptide" title="Tripeptide">Tripeptide</a></li>

<li><a href="Decapeptide" class="mw-redirect" title="Decapeptide">Decapeptide</a></li>

<li><a href="Cyclic_peptide" title="Cyclic peptide">cyclic peptide</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://adisinsight.springer.com/drugs/800032135">"Elamipretide"</a>. <i>AdisInsight</i>. Springer Nature Switzerland AG<span class="reference-accessdate">. Retrieved <span class="nowrap">24 April</span> 2017</span>.</cite></span>

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<li id="cite_note-Chakravarty_2021-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Chakravarty_2021_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Chakravarty_2021_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFChakravartyBhatReddyGupta2021" class="citation book cs1">Chakravarty S, Bhat UA, Reddy RG, Gupta P, Kumar A (January 2021). "Histone deacetylase inhibitors and psychiatric disorders.". <i>Epigenetics in psychiatry</i>. Academic Press. pp. <span class="nowrap">657–</span>699. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-417114-5.00025-5">10.1016/B978-0-12-417114-5.00025-5</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780124171145</bdi>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:82170091">82170091</a>.</cite></span>

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<li id="cite_note-pmid31606087-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid31606087_6-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFOskoChristianson2019" class="citation book cs1">Osko JD, Christianson DW (2019). <i>Methods for the expression, purification, and crystallization of histone deacetylase 6-inhibitor complexes</i>. Methods in Enzymology. Vol. 626. pp. <span class="nowrap">447–</span>474. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fbs.mie.2019.06.028">10.1016/bs.mie.2019.06.028</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780128186695</bdi>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6941440">6941440</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31606087">31606087</a>.</cite></span>

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<li id="cite_note-Loiseau_2002-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Loiseau_2002_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Loiseau_2002_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFLoiseauCavelierNoelGomis2002" class="citation journal cs1">Loiseau N, Cavelier F, Noel JP, Gomis JM (July 2002). "High yield synthesis of tentoxin, a cyclic tetrapeptide". <i>Journal of Peptide Science</i>. <b>8</b> (7): <span class="nowrap">335–</span>346. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fpsc.393">10.1002/psc.393</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12148783">12148783</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:42957097">42957097</a>.</cite></span>

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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"><cite id="CITEREFFarmer2013" class="citation web cs1">Farmer S (2013-10-02). <a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Reactivity_of_Alpha_Hydrogens/Aldol_Reaction">"Aldol Reaction"</a>. <i>Chemistry LibreTexts</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2023-11-11</span></span>.</cite></span>

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<li id="cite_note-Polverino_1997-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Polverino_1997_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Polverino_1997_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFPolverinoPatterson1997" class="citation journal cs1">Polverino AJ, Patterson SD (March 1997). <a rel="nofollow" class="external text" href="https://www.jbc.org/article/S0021-9258(18)41032-0/fulltext">"Selective activation of caspases during apoptotic induction in HL-60 cells. Effects Of a tetrapeptide inhibitor"</a>. <i>The Journal of Biological Chemistry</i>. <b>272</b> (11): <span class="nowrap">7013–</span>7021. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.272.11.7013">10.1074/jbc.272.11.7013</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9054391">9054391</a>.</cite></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"><cite id="CITEREFHazzalinLe_PanseCanoMahadevan1998" class="citation journal cs1">Hazzalin CA, Le Panse R, Cano E, Mahadevan LC (April 1998). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC121414">"Anisomycin selectively desensitizes signalling components involved in stress kinase activation and fos and jun induction"</a>. <i>Molecular and Cellular Biology</i>. <b>18</b> (4): <span class="nowrap">1844–</span>1854. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FMCB.18.4.1844">10.1128/MCB.18.4.1844</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC121414">121414</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9528756">9528756</a>.</cite></span>

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<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite id="CITEREFGuptaPhulara2021" class="citation book cs1">Gupta P, Phulara S (2021). "Chapter 3 - Terpenoids: Types and their application". <i>Biotechnology of Terpenoid Production from Microbial Cell Factories</i>. pp. <span class="nowrap">47–</span>78. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-819917-6.00006-5">10.1016/B978-0-12-819917-6.00006-5</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-12-819917-6</bdi>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:243578830">243578830</a>.</cite></span>

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<li id="cite_note-Luo_2017-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Luo_2017_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Luo_2017_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFLuoWuYangWang2017" class="citation journal cs1">Luo Z, Wu Q, Yang C, Wang H, He T, Wang Y, et al. (February 2017). "A Powerful CD8<sup>+</sup> T-Cell Stimulating D-Tetra-Peptide Hydrogel as a Very Promising Vaccine Adjuvant". <i>Advanced Materials</i>. <b>29</b> (5). <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fadma.201601776">10.1002/adma.201601776</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27859662">27859662</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:33587295">33587295</a>.</cite></span>

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<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><cite id="CITEREFKijimaYoshidaSugitaHorinouchi1993" class="citation journal cs1">Kijima M, Yoshida M, Sugita K, Horinouchi S, Beppu T (October 1993). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2941547-5">"Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase"</a>. <i>The Journal of Biological Chemistry</i>. <b>268</b> (30): <span class="nowrap">22429–</span>22435. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2941547-5">10.1016/S0021-9258(18)41547-5</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8226751">8226751</a>.</cite></span>

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</ol></div></div>

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</style><div id="Hormones57" style="font-size:114%;margin:0 4em"><a href="Hormone" title="Hormone">Hormones</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Endocrine_gland" title="Endocrine gland">Endocrine<br>glands</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Hypothalamic–pituitary250" scope="row" class="navbox-group" style="width:1%"><a href="Hypothalamic%E2%80%93pituitary_hormone" title="Hypothalamic–pituitary hormone">Hypothalamic–<br>pituitary</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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="Hypothalamus" title="Hypothalamus">Hypothalamus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Dopamine" title="Dopamine">Dopamine</a></li>

<li><a href="Somatostatin" title="Somatostatin">Somatostatin (GHIH)</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Posterior_pituitary" title="Posterior pituitary">Posterior pituitary</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="Oxytocin" title="Oxytocin">Oxytocin</a></li>

<li><a href="Vasopressin" title="Vasopressin">Vasopressin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Anterior_pituitary" title="Anterior pituitary">Anterior pituitary</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Prolactin" title="Prolactin">Prolactin</a></li>

<li><a href="Endorphins" title="Endorphins">Endorphins</a></li>

<li><a href="Lipotropin" title="Lipotropin">Lipotropin</a></li></ul></li>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis" title="Hypothalamic–pituitary–adrenal axis">Adrenal axis</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="Adrenal_gland#Adrenal_cortex" title="Adrenal gland">Adrenal cortex</a>

<ul><li><a href="Aldosterone" title="Aldosterone">Aldosterone</a></li>

<li><a href="Cortisol" title="Cortisol">Cortisol</a></li>

<li><a href="Cortisone" title="Cortisone">Cortisone</a></li>

<li><a href="Androstenedione" title="Androstenedione">Androstenedione</a></li></ul></li>

<li><a href="Adrenal_gland#Adrenal_medulla" title="Adrenal gland">Adrenal medulla</a>

<ul><li><a href="Adrenaline" title="Adrenaline">Adrenaline</a></li>

<li><a href="Norepinephrine" title="Norepinephrine">Norepinephrine</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Thyroid" title="Thyroid">Thyroid</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="Thyroid_hormones" title="Thyroid hormones">Thyroid hormones</a>

<li><a href="Calcitonin" title="Calcitonin">Calcitonin</a></li>

<li><a href="Hypothalamic%E2%80%93pituitary%E2%80%93thyroid_axis" title="Hypothalamic–pituitary–thyroid axis">Thyroid axis</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Parathyroid_gland" title="Parathyroid gland">Parathyroid</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">Gonadal axis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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="Testicle" title="Testicle">Testis</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="Testosterone" title="Testosterone">Testosterone</a></li>

<li><a href="Activin_and_inhibin" title="Activin and inhibin">Inhibin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Ovary" title="Ovary">Ovary</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="Estradiol" title="Estradiol">Estradiol</a></li>

<li><a href="Progesterone" title="Progesterone">Progesterone</a></li>

<li><a href="Activin_and_inhibin" title="Activin and inhibin">Activin</a></li>

<li><a href="Activin_and_inhibin" title="Activin and inhibin">Inhibin</a></li>

<li><a href="Relaxin" title="Relaxin">Relaxin</a></li>

<li><a href="Gonadotropin_surge-attenuating_factor" title="Gonadotropin surge-attenuating factor">GnSAF</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Placenta" title="Placenta">Placenta</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Estrogen" title="Estrogen">Estrogen</a></li>

<li><a href="Progesterone" title="Progesterone">Progesterone</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Pancreas" title="Pancreas">Pancreas</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="Glucagon" title="Glucagon">Glucagon</a></li>

<li><a href="Insulin" title="Insulin">Insulin</a></li>

<li><a href="Amylin" title="Amylin">Amylin</a></li>

<li><a href="Somatostatin" title="Somatostatin">Somatostatin</a></li>

<li><a href="Pancreatic_polypeptide" title="Pancreatic polypeptide">Pancreatic polypeptide</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Pineal_gland" title="Pineal gland">Pineal gland</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="Melatonin" title="Melatonin">Melatonin</a></li>

<li><a href="N%2CN-Dimethyltryptamine" class="mw-redirect" title="N,N-Dimethyltryptamine">N,N-Dimethyltryptamine</a></li>

<li><a href="5-Methoxy-N%2CN-dimethyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-dimethyltryptamine">5-Methoxy-N,N-dimethyltryptamine</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" 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="Thymus" title="Thymus">Thymus</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="Thymosin" title="Thymosin">Thymosins</a>

<ul><li><a href="Thymosin_%CE%B11" title="Thymosin α1">Thymosin α1</a></li>

<li><a href="Beta_thymosin" class="mw-redirect" title="Beta thymosin">Beta thymosins</a></li></ul></li>

<li><a href="Thymopoietin" title="Thymopoietin">Thymopoietin</a></li>

<li><a href="Thymulin" title="Thymulin">Thymulin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Digestion" title="Digestion">Digestive system</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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="Stomach" title="Stomach">Stomach</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="Gastrin" title="Gastrin">Gastrin</a></li>

<li><a href="Ghrelin" title="Ghrelin">Ghrelin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Duodenum" title="Duodenum">Duodenum</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Secretin" title="Secretin">Secretin</a></li>

<li><a href="Motilin" title="Motilin">Motilin</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Ileum" title="Ileum">Ileum</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="Enteroglucagon" title="Enteroglucagon">Enteroglucagon</a></li>

<li><a href="Peptide_YY" title="Peptide YY">Peptide YY</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Liver" title="Liver">Liver</a>/other</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="Insulin-like_growth_factor" title="Insulin-like growth factor">Insulin-like growth factor</a>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Adipose_tissue" title="Adipose tissue">Adipose tissue</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="Leptin" title="Leptin">Leptin</a></li>

<li><a href="Adiponectin" title="Adiponectin">Adiponectin</a></li>

<li><a href="Resistin" title="Resistin">Resistin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Human_skeleton" title="Human skeleton">Skeleton</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="Osteocalcin" title="Osteocalcin">Osteocalcin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Kidney" title="Kidney">Kidney</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="Renin" title="Renin">Renin</a></li>

<li><a href="Calcitriol" title="Calcitriol">Calcitriol</a></li>

<li><a href="Prostaglandin" title="Prostaglandin">Prostaglandin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Heart" title="Heart">Heart</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="Natriuretic_peptide" title="Natriuretic peptide">Natriuretic peptide</a>

</div></td></tr></tbody></table><div></div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-06-16" href="https://en.wikipedia.org/wiki/?title=Tetrapeptide&oldid=1295931685">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

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