Synthesis
Tripeptide-1 was synthesized via retrosynthetic analysis.
First, according to the Noyori asymmetric reduction, tripeptide-1 (1) was retrograded to compound ketone 2; ketone 2 can be obtained from compound 4 by selective hydrosilanization to intermediate 3, and then 3 by Tamao-Fleming oxidation; fragment 4 can be cleaved into compounds 5, 6 and commercially available starting material 7, as shown in the figure below:
Then, according to the retrosynthetic analysis, tripeptide 1 was synthesized, and its synthetic route is shown below:
Description
Tripeptide-1 is a small peptide composed of three amino acids (glycine-histidine-lysine or GHK) and is known for type I collagen fragments. When collagen fragment peptides (GHK) are added, it may mistakenly lead the skin to think that collagen has been broken down, resulting in more collagen. Therefore, tripeptide-1 is believed to stimulate collagen production in the skin. More collagen will reduce wrinkles on the face, which will improve the condition of the skin.
Chemical Properties
White powder
Uses
Liver Cell Growth Factor
Uses
Gly-His-Lys acetate salt has been used:
- individually or as a complex with copper to test its effect on cytokines production in the human normal fibroblasts cell lines
- as a model peptide in N,N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl)ammonium betaine based capillary electrophoresis separation studies
- as a component of Coon′s modified Ham′s F-12 medium for culturing Fischer rat thyroid follicular cell line, FRTL-5
General Description
Gly-His-Lys is a tripeptide present at ～200ng/ml in association with α-globulin and albumin, in human blood plasma.
Biochem/physiol Actions
Gly-His-Lys (GHK) acetate salt displays affinity towards copper(II) ions. This property enables GHK to modulate the copper intake into cells. GHK is also involved in quenching toxic by-products generated by lipid peroxidation.
in vitro
In an enzyme assay, the liver growth factor, Tripeptide-1, was hydrolyzed by an aminotripeptidase purified from rat brain cytosol[1].
in vivo
Tripeptide-1 (1% in saline; dose = 10 mg/kg) was injected into the tail vein of male rats (number not specified). Blood samples were collected prior to dosing and for up to 60 minutes post-dosing. Plasma concentration-time profiles of Tripeptide-1 and its l-histidyl-l-lysine metabolite indicated that neither was detected in predose plasma samples. However, after intravenous (IV) injection, Tripeptide-1 was rapidly degraded to l histidyl-l-lysine, rapidly eliminated from circulating blood. It has been reported that Tripeptide-1 is unstable in human plasma and is rapidly degraded by aminopeptidases[1].
References
[1] Wilbur Johnson. “Safety Assessment of Tripeptide-1, Hexapeptide-12, Their Metal Salts and Fatty Acyl Derivatives, and Palmitoyl Tetrapeptide-7 as Used in Cosmetics.” International Journal of Toxicology 37 1 (2018): 102S–90S.
