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Pyroglutamyl-histidyl-glycine

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Pyroglutamyl-histidyl-glycine
Names
IUPAC name 2-amino]propanoyl]amino]acetic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H17N5O5/c19-10-2-1-8(17-10)13(23)18-9(3-7-4-14-6-16-7)12(22)15-5-11(20)21/h4,6-9H,1-3,5H2,(H,15,22)(H,17,19)(H,18,23)(H,20,21)/t7?,8-,9-/m0/s1Key: VTKWFWXOVZIATL-NPPUSCPJSA-N
  • InChI=1/C13H17N5O5/c19-10-2-1-8(17-10)13(23)18-9(3-7-4-14-6-16-7)12(22)15-5-11(20)21/h4,6-9H,1-3,5H2,(H,15,22)(H,17,19)(H,18,23)(H,20,21)/t7?,8-,9-/m0/s1Key: VTKWFWXOVZIATL-NPPUSCPJBL
SMILES
  • O=C2N(C(=O)N(C(=O)NCC(=O)O)CC/1/N=C\N=C\1)CC2
Properties
Chemical formula C13H17N5O5
Molar mass 323.30 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pyroglutamyl-histidyl-glycine (pEHG) is an endogenous tripeptide that acts as a tissue-specific antimitotic and selectively inhibits the proliferation of colon epithelial cells. Early research indicated that pEHG had anorectic effects in mice and was possibly involved in the pathophysiology of anorexia nervosa. However, subsequent studies have found that pEHG lacks anorectic effects and does not alter food intake in mice.

References

  1. Reichelt, WH; Iversen, JG; Paulsen, JE; Elgjo, K; Reichelt, KL (May 2004). "Pyroglutamyl-histidyl-glycine, the endogenous colon mitosis inhibitor, regulates cyclic AMP level in non-tumorigenic colonic epithelial cells". Anticancer Research. 24 (3a): 1465–8. PMID 15274311.
  2. Trygstad, Olav; Foss, Irene; Edminson, Paul D.; Johansen, John H.; Reichelt, Karl L. (1 September 1978). "Humoral Control of Appetite: A Urinary Anorexigenic Peptide. Chromatographic Patterns of Urinary Peptides in Anorexia Nervosa". European Journal of Endocrinology. 89 (1): 196–208. doi:10.1530/acta.0.0890196. PMID 696172.
  3. Bauce, Lorenzo G.; Elliott, Crystal; Hughes, Rhiannon; Goren, H. Joseph (1 January 1981). "Synthesis and assay for activity of a proposed anorexogenic agent, L -pyroglutamyl- L -histidyl-glycine". Canadian Journal of Physiology and Pharmacology. 59 (1): 88–90. doi:10.1139/y81-015. PMID 7214215.
  4. Nance, Dwight M.; Coy, David H.; Kastin, Abba J. (December 1979). "Experiments with a reported anorexigenic tripeptide: PyroGluHisGlyOH". Pharmacology Biochemistry and Behavior. 11 (6): 733–735. doi:10.1016/0091-3057(79)90273-9. PMID 538064. S2CID 30289485.


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