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G4541

Sigma-Aldrich

Gly-Gly-His

≥98% (TLC)

Synonyme(s) :

Copper-binding peptide

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About This Item

Formule empirique (notation de Hill):
C10H15N5O4
Numéro CAS:
7451-76-5
Poids moléculaire :
269.26
Numéro MDL:
MFCD03452928
Code UNSPSC :
12352209
Nomenclature NACRES :
NA.26

product name

Gly-Gly-His,

Pureté

≥98% (TLC)

Forme

solid

Couleur

white

Température de stockage

−20°C

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)

Clé InChI

PDAWDNVHMUKWJR-UHFFFAOYSA-N

Catégories apparentées

Amino Acid Sequence

Gly-Gly-His

Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Gly-Gly-Gly

Ser-Phe-Leu-Leu-Arg-Asn-Pro-Asn-Asp-Lys-Tyr-Glu-Pro-Phe ≥97% (HPLC)

Sigma-Aldrich

S7152

Ser-Phe-Leu-Leu-Arg-Asn-Pro-Asn-Asp-Lys-Tyr-Glu-Pro-Phe

L-Carnosine ~99%, crystalline

Sigma-Aldrich

C9625

L-Carnosine

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
Electrochemical detection of copper using a Gly-Gly-His modified carbon nanotube biosensor
Flavel BS, et al.
Silicon, 3(4) (3)
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
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
A P Dicks et al.
Chemistry & biology, 3(8), 655-659 (1996-08-01)
We have recently shown that S-nitrosothiols (RSNOs) decompose in aqueous buffer to give nitric oxide, an important signalling molecule, and the corresponding disulphides. This occurs by reaction with Cu+ generated from Cu2+ (supplied as hydrated Cu2+) by thiolate reduction. To
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