Glycyl-L-histidyl-L-lysine

Glycyl-L-histidyl-L-lysine, an intricate peptide compound, has enticed the attention of the biomedical realm. The scientific community has rigorously scrutinized its promising utilization in mitigating cardiovascular afflictions, namely hypertension and atherosclerosis. Pioneering hypotheses suggest that this enigmatic entity might operate by orchestrating blood pressure fluctuations and fostering the expanse of vascular well-being. Moreover, ongoing scientific investigations endeavor to unravel the entire gamut of its therapeutic capacities in effectively managing assorted cardiovascular maladies.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: R2012

CAS No:49557-75-7

Synonyms/Alias:glycyl-l-histidyl-l-lysine;49557-75-7;Gly-his-lys;Prezatide;L-Lysine, glycyl-L-histidyl-;Glycyl-histidyl-lysine;Tripeptide-1;Liver cell growth factor;Iamin;Glycylhistidyllysine;KOLLAREN;NSC 379527;ORISTAR GHK;Growth-modulating peptide (human);39TG2H631E;GLY-HIS-LYS-OH;(S)-6-Amino-2-((S)-2-(2-aminoacetamido)-3-(1H-imidazol-4-yl)propanamido)hexanoic acid;Copper Peptide;PC-1020 FREE BASE;C.P.P.;CHEMBL1814493;CHEBI:75430;DTXSID30197831;NSC-379527;Copper(II)ghk;ghk;Copper glycyl-histidyl-lysine;MFCD00036754;UNII-39TG2H631E;Copper Peptide(GHK-Cu, GHK-Copper);C14H24N6O4;Tripeptide-1/GHK;Gly-L-His-L-Lys;Natural Cedarwood Oil;GHK [MI];TRIPEPTIDE-1 [INCI];Seacall Natural Cedarwood Oil;SCHEMBL259085;SCHEMBL19087235;DTXCID90120322;EX-A7713;HY-P0046;BDBM50350478;AKOS016003505;AKOS040758595;DB11296;N(2)-(N-Glycyl-L-histidyl)-L-lysine;1227510-36-2;AC-31946;BG162807;DA-72333;DS-14630;CS-0005654;NS00070865;I10329;Glycyl-L-Histidyl-L-Lysine (H-Gly-L-His-L-Lys-OH);(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanamido]hexanoic acid;(2S)-6-AMINO-2-[(2S)-2-(2-AMINOACETAMIDO)-3-(1H-IMIDAZOL-4-YL)PROPANAMIDO]HEXANOIC ACID;

Chemical Name:(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C14H24N6O4
M.W/Mr.
340.38
Sequence
One Letter Code:GHK
Three Letter Code:H-Gly-His-Lys-OH
Appearance
Solid

Glycyl-L-histidyl-L-lysine is a synthetic tripeptide composed of glycine, histidine, and lysine residues, and is widely recognized for its unique biochemical properties and functional relevance in peptide research. As a small, bioactive peptide, it has garnered significant attention for its role in modulating cellular processes and serving as a model compound in the study of peptide structure-activity relationships. Its distinct sequence and physicochemical characteristics make it a valuable tool for investigating peptide-mediated mechanisms and for supporting a range of research applications in biochemistry, molecular biology, and related scientific fields.

Peptide Mechanism Studies: Glycyl-L-histidyl-L-lysine serves as a model tripeptide for elucidating the molecular mechanisms by which small peptides interact with cellular components. Researchers utilize this compound to probe how peptide sequences influence receptor binding, signal transduction, and cellular uptake. Its defined structure enables the systematic investigation of sequence-specific effects on biological activity, providing insights into the principles governing peptide-receptor interactions and downstream signaling events.

Peptide Synthesis Validation: In the context of synthetic peptide chemistry, this tripeptide is frequently employed as a standard for validating solid-phase peptide synthesis protocols and analytical techniques. Its well-characterized sequence and manageable size make it an ideal reference for optimizing coupling efficiency, assessing resin performance, and calibrating chromatographic or mass spectrometric analyses. The use of such reference peptides is essential for ensuring the reproducibility and reliability of synthetic workflows in peptide laboratories.

Biochemical Assays Development: The tripeptide is commonly incorporated into biochemical assay systems designed to study enzymatic activity, peptide-protein interactions, or substrate specificity. Its modular structure allows for the evaluation of protease cleavage patterns, investigation of binding affinities, and assessment of peptide stability under various experimental conditions. By serving as a defined substrate or probe, it facilitates the development and optimization of sensitive, quantitative assays for high-throughput screening or mechanistic studies.

Cellular Uptake and Transport Research: Glycyl-L-histidyl-L-lysine is also leveraged in studies focused on cellular uptake mechanisms and peptide transport across biological membranes. Its physicochemical properties, including charge distribution and hydrophilicity, provide a basis for exploring how tripeptides traverse cellular barriers, interact with transporters, or are internalized via endocytic pathways. Such research is pivotal for understanding the factors that govern peptide bioavailability and intracellular delivery, particularly in the context of drug delivery system design.

Structure-Activity Relationship (SAR) Analysis: The tripeptide's defined amino acid sequence renders it a valuable tool in structure-activity relationship studies, where systematic modifications to its constituent residues can reveal the impact of sequence variation on biological function. By substituting or altering specific amino acids, researchers can delineate the contributions of individual side chains to binding affinity, activity, or stability. These SAR investigations are fundamental to the rational design of novel peptides with tailored properties for research or industrial applications.

InChI
InChI=1S/C14H24N6O4/c15-4-2-1-3-10(14(23)24)20-13(22)11(19-12(21)6-16)5-9-7-17-8-18-9/h7-8,10-11H,1-6,15-16H2,(H,17,18)(H,19,21)(H,20,22)(H,23,24)/t10-,11-/m0/s1
InChI Key
MVORZMQFXBLMHM-QWRGUYRKSA-N
Canonical SMILES
C1=C(NC=N1)CC(C(=O)NC(CCCCN)C(=O)O)NC(=O)CN
Isomeric SMILES
C1=C(NC=N1)C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)CN

Useful Tools

Peptide Calculator

Abbreviation List

Peptide Glossary

If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.

Featured Services
Peptide Nucleic Acids SynthesisPeptide CDMOEpitope Mapping ServicesPeptide Analysis ServicesCustom Conjugation ServicePeptide Modification ServicesPeptide Synthesis ServicescGMP Peptide Service
Hot Products
About us

Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.

From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.

Our Customers