G4541
Gly-Gly-His
≥98% (TLC)
Synonym(s):
Copper-binding peptide
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About This Item
Empirical Formula (Hill Notation):
C10H15N5O4
CAS Number:
Molecular Weight:
269.26
UNSPSC Code:
12352209
NACRES:
NA.26
MDL number:
Product Name
Gly-Gly-His,
InChI
1S/C10H15N5O4/c11-2-8(16)13-4-9(17)15-7(10(18)19)1-6-3-12-5-14-6/h3,5,7H,1-2,4,11H2,(H,12,14)(H,13,16)(H,15,17)(H,18,19)
InChI key
PDAWDNVHMUKWJR-UHFFFAOYSA-N
assay
≥98% (TLC)
form
solid
color
white
storage temp.
−20°C
Quality Level
SMILES string
[nH]1cnc(c1)CC(NC(=O)CNC(=O)CN)C(=O)O
Related Categories
General description
Gly-Gly-His (GGH) tripeptide with carboxyl-terminal histidine residue is hydrophilic.
Application
Gly-Gly-His has been used:
- as a peptide test probe in the hydrophilic interaction liquid chromatography (HILIC) studies
- in the electrochemical modification of back-side contact transducers (BSC) electrodes in copper (Cu2+) sensing studies
- for the fabrication carbon nanotube electrode for detection of Cu2+ ions
Biochem/physiol Actions
Gly-Gly-His (GGH) tripeptide displays the affinity of copper (Cu2+) complexation. These complexes display good skin tolerance and may be useful in wound healing. GGH copper complexes are proposed to reduce tumor necrosis factor α (TNF-α)-based interleukin 6 (IL-6) secretion by in vivo studies with fibroblasts. GGH is used in comparative studies with other imidazole-containing peptides such as carnosine. An area of active application research involves the GGH binding of copper ions.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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F Tacnet et al.
The Journal of physiology, 465, 57-72 (1993-06-01)
1. The purpose of the present work was to examine certain membrane transport mechanisms likely to carry zinc across the brush-border membrane of pig small intestine, isolated in a vesicular form. 2. In initial velocity conditions, saturation kinetics revealed a
Michael Gerlich et al.
Journal of mass spectrometry : JMS, 48(3), 291-298 (2013-03-16)
Mass spectrometry (MS) is an important analytical technique for the detection and identification of small compounds. The main bottleneck in the interpretation of metabolite profiling or screening experiments is the identification of unknown compounds from tandem mass spectra. Spectral libraries
K C Brown et al.
Biochemistry, 37(13), 4397-4406 (1998-04-29)
The Ni(II) complex of the tripeptide NH2-glycine-glycine-histidine-COOH (GGH) mediates efficient protein-protein cross-linking in the presence of oxidants such as oxone and monoperoxyphthalic acid (MMPP). Here we demonstrate that GGH fused to the amino terminus of a protein can still support
Gly-Gly-His Immobilized On Monolayer Modified Back-Side Contact Miniaturized Sensors for Complexation of Copper Ions
Wawrzyniak UE, et al.
Electroanalysis, 25(6) (25)
Andreza C Matias et al.
Journal of inorganic biochemistry, 116, 172-179 (2012-10-02)
Elevated levels of copper have been detected in various types of human cancer cells, such as breast cancer cells, and a number of mechanisms have been proposed to explain the action and influence of copper on tumor progress. In this
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