Glycyl-histidyl-lysine (GHK) is a quencher of alpha,beta-4-hydroxy-trans-2-nonenal: a comparison with carnosine. insights into the mechanism of reaction by electrospray ionization mass spectrometry, 1H NMR, and computational techniques.

Beretta G, Artali R, Regazzoni L, Panigati M, Facino RM

Chemical research in toxicology3 Aug 2007Cited by 20 (Europe PMC)

PMID17672515DOI10.1021/tx700185sPepBankPUB-17672515

Publisher page PubMedAsk about this study

Summary

The text of this summary is not shown here, because the article license does not allow reuse. Read it at the source (opens in a new tab)

Text rights: Publisher copyright. Results still quote short attributed sentences.

Results from this study6

2 results from studies that gave the peptide. No result from this study comes from people.

01LabIn vitro (cell-free)Mechanism
In phosphate buffer, mass spectrometry and NMR confirmed GHK/HNE adduct formation.
In plain wordsIn lab tests, GHK formed adducts with HNE.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
Not applicableGHK/HNE adduct formation
Study
n: not reported in source
phosphate buffer, pH 7.4
Outcome group
Receptor activity and mechanism · Pharmacology
Studied dose
1 mMAs given in this study.
Source sentences
Summary
We first evaluated the HNE consumption (50 microM, HPLC-UVDAD method) in the presence of GHK (1 mM) in physiomimetic conditions (phosphate buffer, pH 7.4) and confirmed GHK/HNE adduct formation by mass spectrometric analysis (ESI-MS/MS) and (1)H NMR analyses.
Report a problemFND-1767251501
02LabIn vitro (cell-free)Mechanism
In HNE quenching tests, GHK was effective but significantly less potent than carnosine.
In plain wordsIn lab tests, GHK quenched HNE but was significantly less potent than carnosine.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
DecreaseHNE quenching potency
Study
n: not reported in source
HNE quenching assay
Comparator
Carnosine
Outcome group
Receptor activity and mechanism · Pharmacology
Studied dose
1 mMAs given in this study.
Source sentences
Summary
These results indicated that GHK was an effective quencher of HNE, although significantly less potent than the reference compound carnosine
Report a problemFND-1767251502

Studies that did not test the peptide alone4

In this study, GHK (glycyl-L-histidyl-L-lysine) was a lab tool or a carrier, part of a mix, or the subject of a lab method. These results are not evidence about taking GHK (glycyl-L-histidyl-L-lysine).

03Computer modelNot a test of GHK (glycyl-L-histidyl-L-lysine) aloneIn silicoMechanism
In computational reaction analysis, HNE/GHK had lower macrocyclic intermediate stability than HNE/carnosine.
In plain wordsIn computer models, the HNE/GHK intermediate was less stable than the HNE/carnosine intermediate.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
DecreaseMacrocyclic intermediate stability
Study
n: not reported in source
computational reaction analysis
Comparator
HNE/carnosine
Outcome group
Receptor activity and mechanism · Pharmacology
Source sentences
Summary
At a mechanistic level, this explained the different reactivity of the two peptides: (i) The greater stability of the macrocyclic intermediate HNE/carnosine was compared to HNE/GHK.
In this study, GHK (glycyl-L-histidyl-L-lysine) was a lab tool or a carrier, part of a mix, or the subject of a lab method. This result is not evidence about taking GHK (glycyl-L-histidyl-L-lysine).
Report a problemFND-1767251503
04Computer modelNot a test of GHK (glycyl-L-histidyl-L-lysine) aloneIn silicoMechanism
In reaction analysis, GHK had a quasi-folded conformation due to four intramolecular hydrogen bonds.
In plain wordsIn computer models, GHK had a partly folded shape due to four internal hydrogen bonds.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
Not applicableGHK solution conformation
Study
n: not reported in source
computational reaction analysis
Outcome group
Receptor activity and mechanism · Pharmacology
Source sentences
Summary
(ii) GHK in solution has a quasi-folded conformation due to the interaction of four intramolecular hydrogen bonds, three of which need to be broken for the transition state to form (energy barrier, approximately 20 kcal/mol).
In this study, GHK (glycyl-L-histidyl-L-lysine) was a lab tool or a carrier, part of a mix, or the subject of a lab method. This result is not evidence about taking GHK (glycyl-L-histidyl-L-lysine).
Report a problemFND-1767251504
05Computer modelNot a test of GHK (glycyl-L-histidyl-L-lysine) aloneIn silicoMechanism
In computational reaction analysis, GHK had an unfavorable orbital configuration for the intramolecular Michael reaction relative to carnosine.
In plain wordsIn computer models, GHK had a less favorable orbital configuration for the reaction than carnosine.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
Not applicableTransition-state orbital configuration
Study
n: not reported in source
computational reaction analysis
Comparator
Carnosine
Outcome group
Receptor activity and mechanism · Pharmacology
Source sentences
Summary
(iii) The different stereoelectronic features of the transition state lead to the intramolecular Michael reaction, that is, the favorable superimposition of carnosine highest occupied molecular orbital and the HNE lowest unoccupied molecular orbital, in relation to the unfavorable orbital configuration of GHK.
In this study, GHK (glycyl-L-histidyl-L-lysine) was a lab tool or a carrier, part of a mix, or the subject of a lab method. This result is not evidence about taking GHK (glycyl-L-histidyl-L-lysine).
Report a problemFND-1767251505
06Computer modelNot a test of GHK (glycyl-L-histidyl-L-lysine) aloneIn silicoMechanism
In computational reaction analysis, GHK required approximately 20 kcal/mol to form the transition state, compared with approximately 7 kcal/mol for carnosine.
In plain wordsIn computer models, GHK required more energy to form the transition state than carnosine.
Peptide
GHK (glycyl-L-histidyl-L-lysine)
Outcome
IncreaseTransition-state energy barrier
Study
n: not reported in source
computational reaction analysis
Comparator
Carnosine
Outcome group
Receptor activity and mechanism · Pharmacology
Source sentences
Summary
(ii) GHK in solution has a quasi-folded conformation due to the interaction of four intramolecular hydrogen bonds, three of which need to be broken for the transition state to form (energy barrier, approximately 20 kcal/mol).
1 context sentence(design, population, supporting numbers)
Summary · context
By contrast, carnosine, with an extended conformation and only one hydrogen bond, requires less energy to reach the transition state ( approximately 7 kcal/mol).
In this study, GHK (glycyl-L-histidyl-L-lysine) was a lab tool or a carrier, part of a mix, or the subject of a lab method. This result is not evidence about taking GHK (glycyl-L-histidyl-L-lysine).
Report a problemFND-1767251506

AI wrote and checked these results. AI can make mistakes, so check important results against the source.

Version history

PepBank keeps every version of the data on this study. Status changes from Retraction Watch, Europe PMC and Crossref are listed with their source.

Version 2Current
14 Oct 2026, 05:02 UTC
Study results updated
Version 1
14 Oct 2026, 01:46 UTC
First added · source update from Europe PMC

Subjects

Terms as the source lists them.

Publication types

MeSH terms

PepBank is a research reference. Talk to a doctor before you use any peptide.