KPV 10 mg

What is KPV?

KPV is a tripeptide of L-lysine, L-proline and L-valine; the name is made up of the one-letter codes of these three amino acids. The sequence forms the C-terminal end of α-melanocyte-stimulating hormone (α-MSH), which is derived from the precursor protein pro-opiomelanocortin (POMC), and corresponds to positions 11 to 13 there. In the literature KPV is therefore also referred to as α-MSH (11–13) or α-melanotropin (11–13). The same motif occurs at positions 11 to 13 of ACTH, so the name ACTH (11–13) is in use as well.

Structure and key data

• Sequence: H-Lys-Pro-Val-OH (L-lysyl-L-prolyl-L-valine)
• Molecular formula: C16H30N4O4
• Molar mass: 342.43 g/mol (average); monoisotopic mass 342.23 Da
• CAS number: 67727-97-3
• PubChem CID: 125672

These database values describe KPV as the free acid with unmodified chain ends. In native α-MSH, with the sequence SYSMEHFRWGKPV, the ends are modified: the serine at position 1 is acetylated and the valine at position 13 is amidated. When searching PubChem, look for CID 125672, because a plain name search for “KPV” leads to an unrelated compound.

Classification: KPV and the melanocortin analogues

Among the α-MSH-related products in the range, KPV is the shortest. MT1 (Melanotan I) and MT2 (Melanotan II) are synthetic α-MSH analogues with a longer, deliberately modified sequence and are listed in the Melanocortins & Copper Peptides category. KPV, by contrast, takes three amino acids unchanged from the natural sequence. As a section of a larger molecule, it is therefore classified in the Peptide Fragments category, together with BPC-157 and TB-500.

Research context

As a tripeptide, KPV is a substrate of the di- and tripeptide transporter PepT1 (gene SLC15A1). The literature describes uptake via this transporter into intestinal epithelial cells and immune cells. KPV is studied mainly in research on the signalling pathways around NF-κB and MAP kinases. The models used include intestinal epithelial cell lines such as Caco2-BBE and HT29-Cl.19A, the T-cell line Jurkat and preclinical mouse models focusing on the gut. KPV is also discussed as an α-MSH fragment in the context of melanocortin research.

Analytics at GPeptides

For the free acid, mass spectrometry is expected to show the singly protonated ion at about m/z 343.2, derived from the monoisotopic mass of 342.23 Da. A C-terminally amidated variant, as found in native α-MSH, would be just under 1 Da lighter and could thus be distinguished from the free acid. HPLC complements this identity information with the purity value.

KPV, too, is regularly tested externally by an independent laboratory using HPLC and mass spectrometry. The available certificates of analysis are filed in the lab area; products without a published certificate appear there with the status “pending”. What such a document contains is described in the guide How to read a certificate of analysis.