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49557-75-7

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49557-75-7 Usage

Description

Copper peptide GHK-Cu is a naturally occurring copper complex of the tripeptide glycyl-L-histidyl-L-lysine. The tripeptide has strong affinity for copper(II) and was first isolated from human plasma. It can be found also in saliva and urine.

Uses

Different sources of media describe the Uses of 49557-75-7 differently. You can refer to the following data:
1. Copper Peptide(GHK-Cu) can be used as skin antiaging agents.
2. Glycyl-L-histidyl-L-lysine is a liver cell growth factor and an asynthetic hepatotrophic agent that stimulates hepatic erythropoietic factor production.

Definition

ChEBI: A tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence.

Pharmaceutical Applications

Glycyl-l-histidyl-l-lysine (GHK) is a tripeptide known for its high binding affinity to Cu2+ and its complex role in wound healing. The GHK–Cu(II) complex was isolated from human plasma in the 1970s and it was shown to be an activator for wound healing. GHK–Cu(II) has two main functions: as an anti-inflammatory agent to protect the tissue from oxidative damage after the injury, and as an activator for wound healing itself as it activates the tissue remodelling. The structure of GHK is very similar to that of common drugs used to treat ulcers. After the initial stages of wound healing are activated, such as blood coagulation and neutrophil invasion, a second stage of wound healing begins, which includes the population of GHK at the wound, which has a high affinity to Cu2+. Mast cells, which are located in the skin, secrete GHK, which accumulates Cu2+ and forms the copper complex GHK–Cu(II) and therefore increases the metal–tripeptide concentration at the wound. First, GHK–Cu(II) has an anti-inflammatory effect by protecting the tissue from oxidative damage and by suppressing local inflammatory signals (i.e. cytokine interleukin-1 (IL-1)). Second, GHK–Cu(II) is released into the blood stream and encourages the production of wound macrophages that support the wound repair by removing the damaged tissue and secreting a family of several growth factor proteins. GHK–Cu(II) also hinders fibroblast production of TGF-β-1 and therefore suppresses the scar development. The GHK–Cu(II) complex also stimulates the growth of blood vessels, neurons and elastin, and, in general, supports most processes of wound healing.

Check Digit Verification of cas no

The CAS Registry Mumber 49557-75-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,9,5,5 and 7 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 49557-75:
(7*4)+(6*9)+(5*5)+(4*5)+(3*7)+(2*7)+(1*5)=167
167 % 10 = 7
So 49557-75-7 is a valid CAS Registry Number.
InChI:InChI=1/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)

49557-75-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Gly-His-Lys

1.2 Other means of identification

Product number -
Other names Ahk-cu

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:49557-75-7 SDS

49557-75-7Synthetic route

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

Fmoc-His(Trt)-OH
109425-51-6

Fmoc-His(Trt)-OH

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

Conditions
ConditionsYield
Multistep reaction;40%
malondialdehyde
64516-48-9

malondialdehyde

acetaldehyde
75-07-0

acetaldehyde

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

(S)-6-Amino-2-[(S)-2-[2-(3,5-diformyl-4-methyl-4H-pyridin-1-yl)-acetylamino]-3-(1H-imidazol-4-yl)-propionylamino]-hexanoic acid

(S)-6-Amino-2-[(S)-2-[2-(3,5-diformyl-4-methyl-4H-pyridin-1-yl)-acetylamino]-3-(1H-imidazol-4-yl)-propionylamino]-hexanoic acid

Conditions
ConditionsYield
In water at pH 4.2;
biotin pentafluorophenyl ester
120550-35-8

biotin pentafluorophenyl ester

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

C24H38N8O6S

C24H38N8O6S

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 5h;
PEG succinimidyl propionate derivative

PEG succinimidyl propionate derivative

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

PEG-glycyl-L-histidyl-L-lysine

PEG-glycyl-L-histidyl-L-lysine

Conditions
ConditionsYield
at 20℃;
at 20℃;
potassium tetrachloropalladate(II)

potassium tetrachloropalladate(II)

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

[(NH2(CH2CO)NCH(CONHCH(COO)CH2CH2CH2CH2NH3)CH2(CCHNHCHN))PdCl]

[(NH2(CH2CO)NCH(CONHCH(COO)CH2CH2CH2CH2NH3)CH2(CCHNHCHN))PdCl]

Conditions
ConditionsYield
In water acidic soln.;; monitored by (1)H/(13)C-NMR spectroscopy;;
In water-d2 acidic soln.;; monitored by (1)H/(13)C-NMR spectroscopy;;
copper diacetate
142-71-2

copper diacetate

glycyl-L-histidyl-L-lysine
49557-75-7

glycyl-L-histidyl-L-lysine

copper tripeptide-1

copper tripeptide-1

Conditions
ConditionsYield
With sodium methylate In methanol; water at 20℃; for 2h;

49557-75-7Downstream Products

49557-75-7Relevant articles and documents

Solid-phase synthesis, characterization and DNA binding properties of the first chloro(polypyridyl)ruthenium conjugated peptide complex

Karidi, Konstantina,Garoufis, Achilleas,Hadjiliadis, Nick,Reedijk, Jan

, p. 728 - 734 (2005)

A general method for the synthesis of chloro(polypyridyl)ruthenium conjugated peptide complexes via a solid-phase strategy is described. The method is applied to synthesize two positional isomers of the complex [Ru(terpy)(4-CO2H-4'-Mebpy-Gly-L-His-L-LysCONH2)Cl] (PF6). Even though the separation of the isomers was only partially achieved chromatographically, the isomers were unambiguously assigned by NMR spectroscopy. The interactions of the complex [Ru(terpy)(4-CO 2H-4'-Mebpy-Gly-L-His-L-LysCONH2)Cl](PF6) with CT-DNA and plasmid DNA, have been studied with various spectroscopic techniques, showing that (i) the complexes coordinatively bind to DNA preferring the bases guanine and cytosine over the bases thymine and adenine after hydrolysis of the coordinated chloride, (ii) electrostatic interactions between the complex cation and the polyanionic DNA chain assist this binding (iii) only in the case of one isomer the peptide does interact further with DNA as evidenced from 31P NMR spectroscopy, (iv) DNA unwinding occurs in all cases with high binding ratio (Ru/base) values (r > 0.3). The Royal Society of Chemistry 2005.

Solid phase method for synthesis peptide-spacer-lipid conjugates, conjugates synthesized thereby and targeted liposomes containing the same

-

Page 13, (2010/02/03)

A solid phase synthesis method for preparing peptide-spacer-lipid conjugates, the peptide-spacer-lipid conjugates synthesized by the method, and liposomes containing the peptide-spacer-lipid conjugates. The present invention provides a convenient solid phase synthesis method for preparing peptide-spacer-lipid conjugates and provides various linkage groups (such as amide group) for conjugating peptide, spacer and lipid, wherein the spacer may comprise PEG. Several advantages can be achieved, such as the synthetic procedure can be simplified, the synthesis process can be set to automation, the purification is easier in each reaction step, and the product losses can be reduced to minimal during synthesis. The present synthesis method is suitable for preparing a wide range of peptide-spacer-lipid conjugates, provides a peptide-spacer-lipid conjugate prepared by the solid phase synthesis method of the present invention, which can be incorporated into a liposome as the targeting moiety for liposomal drug delivery to specific cells, and provides a targeting liposome containing the present peptide-spacer-lipid conjugate.

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