KPV tripeptide

KPV tripeptide
Identifiers
	IUPAC name (2S)-2-[[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoic acid;
CAS Number	67727-97-3;
PubChem CID	125672;
Chemical and physical data
Formula	C16H30N4O4
Molar mass	342.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N;
	InChI InChI=1S/C16H30N4O4/c1-10(2)13(16(23)24)19-14(21)12-7-5-9-20(12)15(22)11(18)6-3-4-8-17/h10-13H,3-9,17-18H2,1-2H3,(H,19,21)(H,23,24)/t11-,12-,13-/m0/s1; Key:YSPZCHGIWAQVKQ-AVGNSLFASA-N;

KPV tripeptide (Lys-Pro-Val) is a tripeptide derivative that is derived from the C-terminal fragment of alpha-MSH. It has antiinflammatory effects, and is used in skincare products, as well as having been researched for other potential medical applications.^[1]^[2]^[3]^[4]^[5]

References

^ Dalmasso G, Charrier-Hisamuddin L, Nguyen HT, Yan Y, Sitaraman S, Merlin D (January 2008). "PepT1-mediated tripeptide KPV uptake reduces intestinal inflammation". Gastroenterology. 134 (1): 166–178. doi:10.1053/j.gastro.2007.10.026. PMC 2431115. PMID 18061177.
^ Brzoska T, Luger TA, Maaser C, Abels C, Böhm M (August 2008). "Alpha-melanocyte-stimulating hormone and related tripeptides: biochemistry, antiinflammatory and protective effects in vitro and in vivo, and future perspectives for the treatment of immune-mediated inflammatory diseases". Endocrine Reviews. 29 (5): 581–602. doi:10.1210/er.2007-0027. PMID 18612139.
^ Brzoska T, Böhm M, Lügering A, Loser K, Luger TA (2010). "Terminal signal: anti-inflammatory effects of α-melanocyte-stimulating hormone related peptides beyond the pharmacophore". Melanocortins: Multiple Actions and Therapeutic Potential. Advances in Experimental Medicine and Biology. Vol. 681. pp. 107–116. doi:10.1007/978-1-4419-6354-3_8. ISBN 978-1-4419-6353-6. PMID 21222263.
^ Gravina AG, Pellegrino R, Durante T, Palladino G, Imperio G, D'Amico G, et al. (July 2023). "The Melanocortin System in Inflammatory Bowel Diseases: Insights into Its Mechanisms and Therapeutic Potentials". Cells. 12 (14): 1889. doi:10.3390/cells12141889. PMC 10378568. PMID 37508552.
^ Sung J, Ju SY, Park S, Jung WK, Je JY, Lee SJ (August 2025). "Lysine-Proline-Valine peptide mitigates fine dust-induced keratinocyte apoptosis and inflammation by regulating oxidative stress and modulating the MAPK/NF-κB pathway". Tissue & Cell. 95 102837. doi:10.1016/j.tice.2025.102837. PMID 40073467.

[1] Dalmasso G, Charrier-Hisamuddin L, Nguyen HT, Yan Y, Sitaraman S, Merlin D (January 2008). "PepT1-mediated tripeptide KPV uptake reduces intestinal inflammation". Gastroenterology. 134 (1): 166–178. doi:10.1053/j.gastro.2007.10.026. PMC 2431115. PMID 18061177.

[2] Brzoska T, Luger TA, Maaser C, Abels C, Böhm M (August 2008). "Alpha-melanocyte-stimulating hormone and related tripeptides: biochemistry, antiinflammatory and protective effects in vitro and in vivo, and future perspectives for the treatment of immune-mediated inflammatory diseases". Endocrine Reviews. 29 (5): 581–602. doi:10.1210/er.2007-0027. PMID 18612139.

[3] Brzoska T, Böhm M, Lügering A, Loser K, Luger TA (2010). "Terminal signal: anti-inflammatory effects of α-melanocyte-stimulating hormone related peptides beyond the pharmacophore". Melanocortins: Multiple Actions and Therapeutic Potential. Advances in Experimental Medicine and Biology. Vol. 681. pp. 107–116. doi:10.1007/978-1-4419-6354-3_8. ISBN 978-1-4419-6353-6. PMID 21222263.

[4] Gravina AG, Pellegrino R, Durante T, Palladino G, Imperio G, D'Amico G, et al. (July 2023). "The Melanocortin System in Inflammatory Bowel Diseases: Insights into Its Mechanisms and Therapeutic Potentials". Cells. 12 (14): 1889. doi:10.3390/cells12141889. PMC 10378568. PMID 37508552.

[5] Sung J, Ju SY, Park S, Jung WK, Je JY, Lee SJ (August 2025). "Lysine-Proline-Valine peptide mitigates fine dust-induced keratinocyte apoptosis and inflammation by regulating oxidative stress and modulating the MAPK/NF-κB pathway". Tissue & Cell. 95 102837. doi:10.1016/j.tice.2025.102837. PMID 40073467.

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See also

References