Currently, this peptide is synthetically manufactured. The product has not been tested for use in any specific applications or for the presence of DNA. There are a number of different uses in the field of biochemistry. Please see the link below to review the Peer Reviewed Papers available for this item:
https://www.sigmaaldrich.com/search/g4541?focus=papers&page=1&perpage=30&sort=relevance&term=G4541&type=citation_search
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:
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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
1 of 4
This Item | G1887 | G3882 | 50239 |
|---|---|---|---|
| form solid | form - | form powder | form powder |
| assay ≥98% (TLC) | assay ≥97% (TLC) | assay ≥98% (TLC) | assay ≥99.0% (NT) |
| storage temp. −20°C | storage temp. −20°C | storage temp. −20°C | storage temp. - |
| color white | color - | color white to off-white | color white |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
Application
Gly-Gly-His has been used:
- as a peptide test probe in the hydrophilic interaction liquid chromatography (HILIC) studies[1]
- in the electrochemical modification of back-side contact transducers (BSC) electrodes in copper (Cu2+) sensing studies[2]
- for the fabrication carbon nanotube electrode for detection of Cu2+ ions[3]
Biochem/physiol Actions
Gly-Gly-His (GGH) tripeptide displays the affinity of copper (Cu2+) complexation.[2] These complexes display good skin tolerance[2] and may be useful in wound healing.[4] 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.[4] 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.[3]
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Ken Yokawa et al.
Bioscience, biotechnology, and biochemistry, 75(7), 1377-1379 (2011-07-09)
Free divalent ions of copper (Cu) are capable of generating radical species such as hydroxyl radicals in the presence of hydrogen peroxide or ascorbic acid through Harbor-Weiss-like reactions under physiological conditions. It has been reported that radical-mediated damage to DNA
Hirokazu Hamada et al.
Journal of inorganic biochemistry, 101(10), 1529-1536 (2007-08-21)
DNA fiber EPR was used to investigate the DNA binding stabilities and orientations of Cu(II).Gly-Gly-His-derived metallopeptides containing D- vs. L-amino acid substitutions in the first peptide position. This examination included studies of Cu(II).D-Arg-Gly-His and Cu(II).D-Lys-Gly-His for comparison to metallopeptides containing
P C Joshi
Indian journal of biochemistry & biophysics, 35(4), 208-215 (1998-12-17)
Reactive oxygen species (ROS) are considered to play an important role in tissue injury that damages DNA, proteins, carbohydrates and lipids. Increased production of ROS and/or decreased efficiency of antioxidant defense system has been shown to contribute to a number
K C Brown et al.
Biochemistry, 34(14), 4733-4739 (1995-04-11)
The Ni(II) complex of the tripeptide NH2-Gly-Gly-His-COOH is shown to mediate efficient protein-protein cross-linking in the presence of oxidants such as oxone and monoperoxyphthalic acid. Only proteins that associate specifically in solution are cross-linked under these conditions. Preliminary probes of
Electrochemical detection of copper using a Gly-Gly-His modified carbon nanotube biosensor
Flavel BS, et al.
Silicon, 3(4) (3)
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Hi, I have some questions regarding GGH (G4541): 1) is it a synthetic peptide? 2) is it used in molecular biology? 3) Is it DNA free? Thank you in advance. Best regards Maryam
1 answer-
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