Compound monograph
GHK (Prezatide)
GHK is the uncomplexed tripeptide ligand of the GHK-copper complex, identified in 1977 as a growth-modulating tripeptide from human plasma.
01
Identity & nomenclature
GHK is the uncomplexed tripeptide ligand of the GHK-copper complex, identified in 1977 as a growth-modulating tripeptide from human plasma.
GHK, GHK-Cu and Pal-GHK are three different substances: an uncomplexed peptide, a copper coordination species, and a covalently lipidated derivative. CAS 49557-75-7 belongs to THIS entry, the free tripeptide. The copper complex is 89030-95-5. That distinction has practical consequences — certificates of analysis in this market have carried the free-tripeptide number on copper-complex product, which describes the wrong substance.
Declared aliases and development codes: GHK, Glycyl-L-histidyl-L-lysine, Tripeptide-1, NSC-379527.
02
Molecular properties
| Molecular formula | C14H24N6O4 |
|---|---|
| Molecular mass | 340.38 Da |
| CAS Registry Number | 49557-75-7 |
| PubChem CID | 73587 |
| UNII | 39TG2H631E |
| One-letter sequence | GHK |
| Three-letter sequence | Gly–His–Lys–OH |
Three residues with a free N-terminal amine and a free C-terminal carboxyl. No modifications. Copper is NOT part of this entry — see nomenclatureNotes.
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Structural characteristics
Its matrix provenance is sourced: proteolysis of SPARC, a matrix-associated protein, yields KGHK, GHK and longer peptides. That provenance is the basis for its secondary matrikine classification. Two cautions belong with it. Most of the angiogenic activity in that work mapped to KGHK rather than to the GHK tripeptide, and was reported as sequence-specific and apparently independent of bound copper — so neither the longer-fragment results nor a copper dependence should be transferred to GHK. Separately, spectroscopic work on Cu(II) coordination reports three nitrogen atoms and one oxygen in a square-planar arrangement, with the major and minor species present varying by pH. Copper binding is therefore established; a single invariant coordination structure is not.
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Molecular targets & mechanisms
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Analytical considerations
For material specified as uncomplexed GHK, quantitative metal analysis is an identity-relevant measurement rather than a cosmetic one — the peptide ion alone does not establish the absence of copper, and acidic chromatography can change the coordination state before detection. Any experiment described as copper-independent must also account for metals already present in the medium. Neither solution colour nor amino-acid composition establishes the complete identity.
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Verified bibliography
- Growth-modulating serum tripeptide is glycyl-histidyl-lysine.current
Schlesinger DH, Pickart L, Thaler MM
Experientia · 1977-03-15 · Journal Article
- SPARC is a source of copper-binding peptides that stimulate angiogenesis.current
Lane TF, Iruela-Arispe ML, Johnson RS, Sage EH
The Journal of cell biology · 1994-05 · Journal Article
- N.m.r. and e.p.r. investigation of the interaction of copper(II) and glycyl-L-histidyl-L-lysine, a growth-modulating tripeptide from plasma.current
Laussac JP, Haran R, Sarkar B
The Biochemical journal · 1983-02-01 · Journal Article
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Methodology & citation verification
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