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Merck
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Key Documents

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:
Peso molecular:
269.26
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.26

product name

Gly-Gly-His,

assay

≥98% (TLC)

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

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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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
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
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
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

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