Pyroglutamyl-histidyl-glycine

Pyroglutamyl-histidyl-glycine (pEHG) is an endogenous tripeptide that acts as a tissue-specific antimitotic and selectively inhibits the proliferation of colon epithelial cells.[1] Early research indicated that pEHG had anorectic effects in mice and was possibly involved in the pathophysiology of anorexia nervosa.[2] However, subsequent studies have found that pEHG lacks anorectic effects and does not alter food intake in mice.[3][4]

Pyroglutamyl-histidyl-glycine
Names
IUPAC name
2-[[(2S)-3-(4H-imidazol-4-yl)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]acetic acid
Identifiers
3D model (JSmol)
ChemSpider
  • 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/s1 checkY
    Key: VTKWFWXOVZIATL-NPPUSCPJSA-N checkY
  • 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/s1
    Key: VTKWFWXOVZIATL-NPPUSCPJBL
  • O=C2N[C@H](C(=O)N[C@H](C(=O)NCC(=O)O)CC/1/N=C\N=C\1)CC2
Properties
C13H17N5O5
Molar mass 323.30 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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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