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G1887

Sigma-Aldrich

Gly-His-Lys acetate salt

≥97% (TLC)

Synonym(s):

Liver cell growth factor

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About This Item

Linear Formula:
C14H24N6O4C2H4O2
CAS Number:
72957-37-0
Molecular Weight:
400.43
MDL number:
MFCD00012699
UNSPSC Code:
51111800
PubChem Substance ID:
24894913
NACRES:
NA.32

Assay

≥97% (TLC)

composition

Peptide content, ~70%

storage temp.

−20°C

SMILES string

CC(O)=O.NCCCC[C@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)CN)C(O)=O

InChI

1S/C14H24N6O4.C2H4O2/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;1-2(3)4/h7-8,10-11H,1-6,15-16H2,(H,17,18)(H,19,21)(H,20,22)(H,23,24);1H3,(H,3,4)/t10-,11-;/m0./s1

InChI key

MGNUTAFMLGJBGV-ACMTZBLWSA-N

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Amino Acid Sequence

Gly-His-Lys

General description

Gly-His-Lys is a tripeptide present at ∼200ng/ml in association with α-globulin and albumin, in human blood plasma.

Application

Gly-His-Lys (GHK) has been used for the preparation of post-operative intra-articular injection of GHK-Cu (copper).
Gly-His-Lys acetate salt has been used:
  • individually or as a complex with copper to test its effect on cytokines production in the human normal fibroblasts cell lines
  • as a model peptide in N,N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl)ammonium betaine based capillary electrophoresis separation studies
  • as a component of Coon′s modified Ham′s F-12 medium for culturing Fischer rat thyroid follicular cell line, FRTL-5

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L Pickart et al.
Journal of chromatography, 175(1), 65-73 (1979-07-11)
Isolation and purification of growth-modulating peptides from biological sources is often accompanied by excessive losses of bioactive material. During the isolation of a growth-modulating tripeptide glycylhistidyllysine (GHL) from human plasma, copper and iron were found to co-isolate with the peptide.
Growth-modulating human plasma tripeptide: relationship between molecular structure and DNA synthesis in hepatoma cells.
L Pickart et al.
FEBS letters, 104(1), 119-122 (1979-08-01)
Sai-Chuen Fu et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 33(7), 1024-1033 (2015-03-04)
After anterior cruciate ligament reconstruction (ACLR), the biological healing of the graft is a rate-limiting step which can contribute to graft failure. The tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu(II) (GHK-Cu) is a well-known activator of tissue remodeling. We investigated whether GHK-Cu can improve
Jingyuan Xiong et al.
Drug and chemical toxicology, 41(4), 501-508 (2017-11-17)
Thyroid hormones are involved in many important physiological activities including regulation of energy metabolism, development of nervous system, maintenance of cerebral functions, and so on. Endocrine-disrupting chemicals (EDCs) that interfere with thyroid functions raise serious concerns due to their frequent
A Siméon et al.
Life sciences, 67(18), 2257-2265 (2000-10-25)
Glycyl-histidyl-lysine-Cu2+ (GHK-Cu) is a tripeptide-copper complex known to be a potent wound healing agent. We previously showed its ability to stimulate in vitro and in vivo the synthesis of extracellular matrix components. The aim of this study was to determine
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