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72957-37-0

72957-37-0 Structure

72957-37-0 Structure
IdentificationMore
[Name]

GLY-HIS-LYS ACETATE SALT
[CAS]

72957-37-0
[Synonyms]

GLYCYL-L-HISTIDYL-L-LYSINE ACETATE
GLY-HIS-LYS ACETATE
GLY-HIS-LYS ACETATE SALT
GLY-HIS-LYS ACOH H2O
H-GLY-HIS-LYS-OH ACETATE SALT
H-GLY-HIS-LYS-OH ACOH
LIVER CELL GROWTH FACTOR
LIVER CELL GROWTH FACTOR ACETATE SALT
LIVER-CELL GROWTH FACTOR ACOH H2O
N2-(N-glycyl-L-histidyl)-L-lysine monoacetate
GLY-HIS-LYS ACETATE CELL CULTURE TESTED
GLYCYL-L-HISTIDYL-L-LYSIN ACETAT HYDRAT
GLYCINE-L-HISTIDINE-L-LYSINE extrapure
[EINECS(EC#)]

277-125-4
[Molecular Formula]

C16H28N6O6
[MDL Number]

MFCD00012699
[Molecular Weight]

400.43
[MOL File]

72957-37-0.mol
Questions And AnswerBack Directory
[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:
Retrosynthetic Analysis of Tripeptide 1
Then, according to the retrosynthetic analysis, tripeptide 1 was synthesized, and its synthetic route is shown below:
Synthesis of tripeptide-1

Chemical PropertiesBack Directory
[storage temp. ]

−20°C
[form ]

powder
[color ]

white
[biological source]

synthetic (organic)
[Water Solubility ]

H2O: soluble 0.5mg/mL, clear, colorless
[Sequence]

Gly-His-Lys
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
ANTIOXIDANT
SKIN PROTECTING
[InChIKey]

MGNUTAFMLGJBGV-ACMTZBLWSA-N
[SMILES]

C(=O)(O)C.[C@@H](NC(=O)CN)(C(=O)N[C@H](C(=O)O)CCCCN)CC1N=CNC=1 |&1:4,13,r|
[CAS DataBase Reference]

72957-37-0(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[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
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

GLY-HIS-LYS ACETATE SALT(72957-37-0)MS
GLY-HIS-LYS ACETATE SALT(72957-37-0)IR1
GLY-HIS-LYS ACETATE SALT(72957-37-0)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

72957-37-0(sigmaaldrich)
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