copper tripeptide comes up often in conversation and rarely with the context attached. Here we lay out the basics in order, then work through the practical considerations.
Last reviewed on 2026-05-27. Where a claim depends on a specific study, the study is described rather than over-claimed.
The sequence now called GHK was first reported in the early 1970s after isolation from human plasma, where it was noted to influence liver cell behavior in laboratory preparations. Later work described a copper-binding form and its activity in fibroblast and wound-model experiments. Review articles frequently group the substance with other copper peptides. Concentrations in blood appear to fall with age in several small surveys, although the reason for this trend is not settled. Whether such a decline carries functional consequences remains an open question.
Published work on GHK-Cu concentrates largely on cell culture systems rather than whole organisms. Frequently used endpoints include collagen synthesis, expression of matrix metalloproteinases, and migration of fibroblasts. Some reports describe antioxidant behavior, while others stress delivery of copper into cells. These mechanisms are proposed rather than demonstrated, and the relative weight of each pathway is unclear. Human trials are few and generally small, so laboratory findings should not be read as confirmed clinical results.
GHK-Cu is a coordination complex formed between the tripeptide glycyl-L-histidyl-L-lysine and a copper(II) ion. The peptide backbone consists of glycine, histidine, and lysine joined in that order. Copper is held through the imidazole nitrogen of histidine and the alpha-amino group at the N-terminus, which together produce a square-planar arrangement around the metal center. The solid appears blue to violet, a color that originates from d-d electronic transitions within the copper coordination sphere. The complex is indexed under CAS number 89030-95-5.
GHK-Cu is the copper-binding complex formed by the tripeptide glycyl-L-histidyl-L-lysine and a copper(II) ion. The free peptide is usually written as GHK, and the complex is written as GHK-Cu or Cu-GHK. The sequence was identified in human plasma and later detected in saliva and urine. Its name comes from the single-letter codes of glycine, histidine and lysine. The complex is widely described as a naturally occurring carrier of copper in blood rather than as a free peptide with its own hormonal role.
Copper binds to the peptide through the histidine imidazole nitrogen and the terminal amino group, forming a stable square-planar complex. Binding constants reported for copper(II) with GHK are high, so the peptide competes effectively for copper in solution. The complex absorbs visible light, which gives solutions a blue to violet colour. Whether the metal-free peptide has a distinct biological function of its own is still an open question; some work treats it mainly as a copper delivery vehicle, while other work reports peptide-specific effects.
| Property | Value | Notes |
|---|---|---|
| Chemical class | Copper(II) peptide complex | Peptide chain coordinated to a single metal ion |
| CAS number | 89030-95-5 | Indexed for the peptide-copper complex |
| Molecular formula | C14H22CuN6O4 | Approximate formula for a one-to-one complex |
| Appearance | Blue to violet solid | Color from copper d-d transitions |
| Solubility class | Freely soluble in water | Also dispersible in some polar solvents |
Characterizing GHK-Cu requires methods that distinguish the intact complex from free peptide and unbound copper. UV-visible absorption around 600 nm provides a rapid check for copper coordination, while circular dichroism reports on peptide secondary structure. Mass spectrometry confirms the peptide mass and can detect copper adducts under carefully controlled conditions. Electron paramagnetic resonance is particularly informative for Cu(II) because it reveals the ligand field symmetry. No single technique fully defines the complex, so laboratories combine orthogonal methods.
Stability of GHK-Cu in solution depends on pH, temperature, buffer composition, and oxygen exposure. The copper center can undergo reduction or dissociation, especially in the presence of strong metal chelators such as EDTA. Aqueous solutions are often prepared fresh or stored frozen to limit degradation. Lyophilized solid is more stable than liquid formulations, but it can absorb moisture and should be kept dry. Light exposure may also affect copper complexes, though the effect is often modest.
Purity assessment typically involves high-performance liquid chromatography for the peptide and atomic spectroscopy for copper content. The ratio of copper to peptide is a key quality parameter; a value near one indicates proper stoichiometry. Impurities can include free peptide, copper salts, and truncated sequences from synthesis. Because the complex is dynamic, sample preparation and mobile-phase conditions can shift the observed species. Reported purity values therefore depend on the analytical method and should be interpreted with that context.
Solutions of GHK-Cu respond strongly to pH, redox conditions, and the presence of competing chelators such as EDTA. Below roughly pH 4 the copper tends to dissociate, because the amide nitrogen donors become protonated and can no longer coordinate. Strongly alkaline conditions instead favour hydrolysis and precipitation of copper hydroxide. Dissolved oxygen and light accelerate breakdown of the peptide backbone, and the copper released during that process can catalyse further oxidation, so dry, cold, dark storage is the usual recommendation.
Routine characterisation relies on reversed-phase high-performance liquid chromatography for peptide purity, paired with mass spectrometry for identity confirmation. Ultraviolet-visible spectroscopy detects the metal centre through its absorption band in the visible region, and inductively coupled plasma mass spectrometry quantifies total copper so that a metal-to-peptide ratio can be calculated. Amino acid analysis confirms the expected residue composition. Together these techniques establish concentration, identity, and stoichiometry, but none of them directly reports biological activity.
Analytical verification commonly relies on high-performance liquid chromatography for purity assessment and mass spectrometry for identity confirmation. Spectroscopic methods such as UV-visible absorption and electron paramagnetic resonance can probe the metal centre itself, since the d9 configuration of copper(II) produces characteristic signals. Elemental analysis or plasma-based techniques quantify copper content. Because each method reports a different aspect of the same sample, purity figures are most meaningful when the technique and its detection wavelength are stated alongside the value.
Stability of the complex in solution depends on pH, temperature, and the presence of competing ligands. It is generally described as more resistant to breakdown than the metal-free chain, since coordination reduces susceptibility to enzymatic attack. Oxidation and hydrolysis can nevertheless proceed over time in aqueous media. Storage guidance in laboratory settings commonly involves refrigeration, protection from light, and avoidance of strongly alkaline conditions. Published data on long-term behaviour vary considerably and depend on the specific matrix.
Handling practices for the solid material emphasise low temperature and dryness. The lyophilised or powdered form is typically kept at refrigerator or freezer temperatures together with a desiccant. Working solutions are often prepared fresh, because repeated freeze-thaw cycles and extended storage may alter the complex. Glass or inert plastic containers are preferred over materials that could leach metal ions into the preparation. Such practices follow general peptide conventions rather than substance-specific regulations.
Dry material is normally held cold, commonly at -20 °C for long-term storage and 2 to 8 °C for working quantities, protected from light and moisture. Vials should be allowed to reach room temperature before opening so that condensation does not form on the powder. In liquid formulations the complex is generally kept near neutral to slightly acidic pH, because strongly alkaline conditions favour precipitation of copper hydroxide. Antioxidants or chelate-stabilising excipients are often added, though the specific approaches are proprietary and rarely published in detail.
Identity and purity are assessed mainly by reversed-phase high-performance liquid chromatography with ultraviolet detection, often paired with mass spectrometry to confirm the expected mass. Copper content is measured separately by inductively coupled plasma optical emission spectrometry or atomic absorption spectroscopy, because the peptide assay alone does not establish the metal-to-peptide ratio. Visible spectroscopy provides a rapid check on complex integrity through the absorption band in the visible region. Agreement between the peptide assay and the copper assay is the practical test of whether a sample is the intended complex rather than a mixture.
Tositumomab – Bexxar – 2003 – CD20 Mogamulizumab – Poteligeo – August 2018 – CCR4 Moxetumomab pasudotox – Lumoxiti – September 2018 – CD22 Cemiplimab – Libtayo – September 2018 – PD-1 Polatuzumab vedotin – Polivy – June 2019 – CD79B The bispecific antibodies have arrived in the clinic. In 2009, the bispecific antibody catumaxomab was approved in the European Union and was later withdrawn for commercial reasons. Others include amivantamab, blinatumomab, teclistamab, and emicizumab.
==== Nitriles from glucosinolates in cruciferous plants ==== An important group of natural products that serve as precursors of nitriles are the mustard oil glycosides (glucosinolates), which are biosynthesized analogously to direct nitrile formation via an aldoxime intermediate. Glucosinolates constitute a major class of secondary metabolites produced by plants of the cruciferous family (Brassicaceae) for defense against herbivores and microorganisms. Normally, glucosinolates are hydrolyzed by myrosinase to isothiocyanates; however, in the presence of an additional protein (epithio specifier protein), nitriles are formed instead. Sinigrin is found primarily in horseradish, wasabi, and brown mustard, but also in head cabbage, kale, cauliflower, and Brussels sprouts; in addition to allyl isothiocyanate, it can be degraded to allyl cyanide (3-butenenitrile). Glucotropaeolin, present in garden cress, is degraded to phenylacetonitrile; gluconasturtiin, found in watercress, is degraded to 3-phenylpropionitrile. Sinalbin, occurring in Lepidium draba, can analogously be degraded to 4-hydroxyphenylacetonitrile.
=== Solvation effects === Solvation significantly affects the basicity of amines. N−H groups strongly interact with water, especially in ammonium ions. Consequently, the basicity of ammonia is enhanced by 1011 by solvation. The intrinsic basicity of amines, i.e. the situation where solvation is unimportant, has been evaluated in the gas phase. In the gas phase, amines exhibit the basicities predicted from the electron-releasing effects of the organic substituents. Thus tertiary amines are more basic than secondary amines, which are more basic than primary amines, and finally ammonia is least basic. The order of pKb values (basicities in water) does not follow this order. Similarly, aniline is more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution. In aprotic polar solvents such as DMSO, DMF, and acetonitrile the energy of solvation is not as high as in protic polar solvents like water and methanol. For this reason, the basicity of amines in these aprotic solvents is almost solely governed by the electronic effects.
Sources: en.wikipedia.org
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=== EC 1.17.4 With a disulfide as acceptor === EC 1.17.4.1: ribonucleoside-diphosphate reductase EC 1.17.4.2: ribonucleoside-triphosphate reductase (thioredoxin) EC 1.17.4.3: transferred to EC 1.17.7.1, (E)-4-hydroxy-3-methylbut-2-enyl-diphosphate synthase. EC 1.17.4.4: vitamin-K-epoxide reductase (warfarin-sensitive) EC 1.17.4.5: vitamin-K-epoxide reductase (warfarin-insensitive)
=== PE Applied Biosystems === In September 1995, Tony L. White from Baxter International Inc. became president and chief executive officer of Perkin-Elmer. In 1996 the company was reorganized into two separate operating divisions, Analytical Instruments and PE Applied Biosystems. The PE Applied Biosystems division accounted for half of Perkin-Elmer's total revenue, with net revenues up by 26%. In 1997, revenues reached almost US$1.3 billion, of which PE Applied Biosystems was US$653 million. The company acquired GenScope, Inc., and Linkage Genetics, Inc. The Linkage Genetics unit was combined with Zoogen to form PE AgGen, focused on genetic analysis services for plant and animal breeding. The PE Applied Biosystems division partnered with Hyseq, Inc., for work on the new DNA chip technology, and also worked with Tecan U.S., Inc., on combinatorial chemistry automation systems, and also with Molecular Informatics, Inc. on genetic data management and analysis automated systems.
Sources: en.wikipedia.org
It is the copper complex of the tripeptide glycyl-L-histidyl-lysine. The metal ion is held by the histidine imidazole group and the peptide N-terminus. Most research on it concerns skin and wound models.
The tripeptide was first isolated from human plasma and has also been reported in saliva and urine. Plasma levels appear to decline with age in some small studies. Those observations rest on limited sample sizes.
It is not authorized as a systemic medicine in most countries. Cosmetic preparations list it as an ingredient rather than an active pharmaceutical substance. Legal status therefore differs by jurisdiction.
The letters GHK are the one-letter codes for glycine, histidine and lysine, the three amino acids in the peptide. The suffix Cu indicates that the peptide is bound to a copper ion, normally copper(II).