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Merck
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Documentos clave

G4541

Sigma-Aldrich

Gly-Gly-His

≥98% (TLC)

Sinónimos:

Copper-binding peptide

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About This Item

Fórmula empírica (notación de Hill):
C10H15N5O4
Número de CAS:
7451-76-5
Peso molecular:
269.26
MDL number:
MFCD03452928
UNSPSC Code:
12352209
NACRES:
NA.26

product name

Gly-Gly-His,

assay

≥98% (TLC)

Quality Level

200

form

solid

color

white

storage temp.

−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)

InChI key

PDAWDNVHMUKWJR-UHFFFAOYSA-N

Categorías relacionadas

Amino Acid Sequence

Gly-Gly-His

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
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
Meng Lin et al.
Biosensors & bioelectronics, 26(2), 940-945 (2010-07-16)
We developed a novel biosensor comprising a transducer of carboxyl end-capped overoxidized polypyrrole nanowire electrode and a probe of tripeptide (Gly-Gly-His) selectively cognitive of Cu2+. The developed sensor was demonstrated to specifically detect Cu2+ in the nanomolar range. The diameter
Electrochemical detection of copper using a Gly-Gly-His modified carbon nanotube biosensor
Flavel BS, et al.
Silicon, 3(4) (3)
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
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