P2053
pGlu-Glu-Pro Amide
≥97% (HPLC)
Synonym(s):
Fertilization Promoting Peptide
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About This Item
Empirical Formula (Hill Notation):
C15H22N4O6
CAS Number:
Molecular Weight:
354.36
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
InChI
1S/C15H22N4O6/c16-13(23)10-2-1-7-19(10)15(25)9(4-6-12(21)22)18-14(24)8-3-5-11(20)17-8/h8-10H,1-7H2,(H2,16,23)(H,17,20)(H,18,24)(H,21,22)
SMILES string
NC(=O)C1CCCN1C(=O)C(CCC(O)=O)NC(=O)C2CCC(=O)N2
InChI key
HYZBGWLLSXSYLX-UHFFFAOYSA-N
assay
≥97% (HPLC)
storage temp.
−20°C
Biochem/physiol Actions
TRH analog that is produced in the thyroid, mammary gland and prostate. Promotes fertilization by enhancing sperm function.
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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Katalin Prokai-Tatrai et al.
Bioorganic & medicinal chemistry letters, 13(6), 1011-1014 (2003-03-20)
Potential prodrugs for the TRH-like tripeptide pGlu-Glu-Pro-NH(2) were synthesized either by esterifying the Glu side-chain of the parent peptide in solution with alcohols in the presence of resin-bound dicyclohexylcarbodiimide or by solid-phase peptide chemistry. Affinities of these ester prodrugs to
Lynn R Fraser et al.
Molecular human reproduction, 9(12), 739-748 (2003-11-14)
When placed in a suitable environment, mammalian spermatozoa begin to capacitate and continue until fully capacitated; in vitro, some will 'over-capacitate' and undergo spontaneous acrosome loss, undesirable since acrosome-reacted cells are non-fertilizing. Seminal plasma contains several molecules able to bind
K Prokai-Tatrai et al.
Medicinal chemistry (Shariqah (United Arab Emirates)), 1(2), 141-152 (2006-06-22)
A metabolically stable and centrally acting analog of pGlu-Glu-Pro-NH2 ([Glu2]TRH, a tripeptide structurally related to TRH (thyrotropin-releasing hormone)) was designed by replacing the amino-terminal pyroglutamyl residue with a pyridinium moiety. The analeptic action of the analog was used to optimize
Albert Eugene Pekary et al.
Brain research, 1125(1), 67-76 (2006-11-23)
This is the first report of diurnal variations in the levels of thyrotropin-releasing hormone-like peptides (pGlu-X-Pro-NH(2), where "X" can be any amino acid residue) in brain regions involved in mood regulation. These peptides have neuroprotective and antidepressant-like properties that may
Vien Nguyen et al.
Neuroscience letters, 415(1), 64-67 (2007-01-20)
Local perfusion of pGlu-Glu-Pro-NH2, an endogenous peptide structurally related to thyrotropine-releasing hormone (TRH), via in vivo microdialysis into the rat hippocampus did not change the basal level of extracellular acetylcholine. However, co-perfusion of pGlu-Glu-Pro-NH2 with TRH in equimolar concentrations yielded
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