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49557-75-7,MFCD00036754
Catalog No.:AA00I8S3

49557-75-7 | Glycyl-l-histidyl-l-lysine

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1mg
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in stock  
$6.00   $4.00
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250mg
98%
in stock  
$14.00   $10.00
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1g
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$42.00   $29.00
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5g
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I8S3
Chemical Name:
Glycyl-l-histidyl-l-lysine
CAS Number:
49557-75-7
Molecular Formula:
C14H24N6O4
Molecular Weight:
340.3782
MDL Number:
MFCD00036754
SMILES:
NCCCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1nc[nH]c1)NC(=O)CN
Properties
Computed Properties
 
Complexity:
434  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
11  
XLogP3:
-4.4  

Upstream Synthesis Route

[1]DaltonTransactions,2005,#4,p.728-734

Downstream Synthesis Route
64516-48-9    75-07-0    49557-75-7   
(S)-6-Amino-2-(S)-2-2-(3,5-diformyl-4-methyl-4H-pyridin-1-yl)-acetylamino-3-(1H-imidazol-4-yl)-propionylamino-hexanoicacid 

[1]Tetrahedron,1988,vol.44,p.2793

[1]DaltonTransactions,2005,p.728-734

120550-35-8    49557-75-7   
C24H38N8O6S 

[1]LifeSciences,2007,vol.80,p.275-284

Literature

Title: GHK Peptide as a Natural Modulator of Multiple Cellular Pathways in Skin Regeneration.

Journal: BioMed research international 20150101

Title: Stem cell recovering effect of copper-free GHK in skin.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20121101

Title: Thermodynamic study of Cu2+ binding to the DAHK and GHK peptides by isothermal titration calorimetry (ITC) with the weaker competitor glycine.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20120101

Title: The human tripeptide GHK-Cu in prevention of oxidative stress and degenerative conditions of aging: implications for cognitive health.

Journal: Oxidative medicine and cellular longevity 20120101

Title: Effect of Gly-Gly-His, Gly-His-Lys and their copper complexes on TNF-alpha-dependent IL-6 secretion in normal human dermal fibroblasts.

Journal: Acta poloniae pharmaceutica 20120101

Title: In vitro evaluation of compression-coated glycyl-L-histidyl-L-lysine-Cu(II) (GHK-Cu2+)-loaded microparticles for colonic drug delivery.

Journal: Drug development and industrial pharmacy 20111101

Title: X-ray and solution structures of Cu(II) GHK and Cu(II) DAHK complexes: influence on their redox properties.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20110829

Title: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping.

Journal: Bioorganic & medicinal chemistry 20110801

Title: Human skin penetration of a copper tripeptide in vitro as a function of skin layer.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20110101

Title: Synthesis and biological evaluation of [(18)F]tetrafluoroborate: a PET imaging agent for thyroid disease and reporter gene imaging of the sodium/iodide symporter.

Journal: European journal of nuclear medicine and molecular imaging 20101101

Title: Human skin retention and penetration of a copper tripeptide in vitro as function of skin layer towards anti-inflammatory therapy.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20101101

Title: Copper.Lys-Gly-His-Lys mediated cleavage of tRNA(Phe): studies of reaction mechanism and cleavage specificity.

Journal: Journal of inorganic biochemistry 20090601

Title: Overexpression of USF increases TGF-beta1 protein levels, but G1 phase arrest was not induced in FRTL-5 cells.

Journal: Journal of Korean medical science 20081001

Title: Acrolein sequestering ability of the endogenous tripeptide glycyl-histidyl-lysine (GHK): characterization of conjugation products by ESI-MSn and theoretical calculations.

Journal: Journal of pharmaceutical and biomedical analysis 20080715

Title: Regulation of inhibitors of differentiation family proteins by thyroid-stimulating hormone in FRTL-5 thyroid cells.

Journal: Journal of Korean medical science 20080401

Title: Could chronic wounds not heal due to too low local copper levels?

Journal: Medical hypotheses 20080101

Title: Biological activities of selected peptides: skin penetration ability of copper complexes with peptides.

Journal: Journal of cosmetic science 20080101

Title: Understanding marine mussel adhesion.

Journal: Marine biotechnology (New York, N.Y.) 20071201

Title: 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.

Journal: Chemical research in toxicology 20070901

Title: In vitro observations on the influence of copper peptide aids for the LED photoirradiation of fibroblast collagen synthesis.

Journal: Photomedicine and laser surgery 20070601

Title: ESI-MS study of the mechanism of glycyl-l-histidyl-l-lysine-Cu(II) complex transport through model membrane of stratum corneum.

Journal: Talanta 20070430

Title: A therapeutic approach for diabetic wound healing using biotinylated GHK incorporated collagen matrices.

Journal: Life sciences 20070102

Title: Evaluation of the effects of topical tripeptide-copper complex and zinc oxide on open-wound healing in rabbits.

Journal: Veterinary dermatology 20061201

Title: UbcH10 overexpression may represent a marker of anaplastic thyroid carcinomas.

Journal: British journal of cancer 20050822

Title: Effects of copper tripeptide on the growth and expression of growth factors by normal and irradiated fibroblasts.

Journal: Archives of facial plastic surgery 20050101

Title: Formation equilibria of nickel complexes with glycyl-histidyl-lysine and two synthetic analogues.

Journal: Journal of inorganic biochemistry 20040101

Title: [Pharmacological correction of immuno-metabolic disorders with the peptide Gly-His-Lys in hepatic damage induced by tetrachloromethane].

Journal: Patologicheskaia fiziologiia i eksperimental'naia terapiia 20030101

Title: The effect of topical tripeptide-copper complex on healing of ischemic open wounds.

Journal: Veterinary surgery : VS 20030101

Title: Isolation of a normal human thyroid cell line: hormonal requirement for thyroglobulin regulation.

Journal: Thyroid : official journal of the American Thyroid Association 20020701

Title: Testosterone and estradiol differentially regulate TSH-induced thyrocyte proliferation in immature and adult rats.

Journal: Steroids 20020601

Title: Tripeptide Gly-His-Lys is a hepatotropic immunosuppressor.

Journal: Bulletin of experimental biology and medicine 20020601

Title: A new fluorescent chemosensor for copper ions based on tripeptide glycyl-histidyl-lysine (GHK).

Journal: Organic letters 20011018

Title: Copper complexes of glycyl-histidyl-lysine and two of its synthetic analogues: chemical behaviour and biological activity.

Journal: Biochimica et biophysica acta 20010503

Title: The tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+ stimulates matrix metalloproteinase-2 expression by fibroblast cultures.

Journal: Life sciences 20000922

Title: Simultaneous determination of glycyl-L-histidyl-L-lysine and its metabolite, L-histidyl-L-lysine, in rat plasma by high-performance liquid chromatography with post-column derivatization.

Journal: Journal of chromatography. B, Biomedical sciences and applications 19970425

Title: Binding of the growth factor glycyl-L-histidyl-L-lysine by heparin.

Journal: FEBS letters 19951204

Title: In vivo stimulation of connective tissue accumulation by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+ in rat experimental wounds.

Journal: The Journal of clinical investigation 19931101

Title: Stimulation of sulfated glycosaminoglycan synthesis by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+.

Journal: Life sciences 19920101

Title: Stimulation of collagen synthesis in fibroblast cultures by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+.

Journal: FEBS letters 19881010

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