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Gliadorphin
Names
IUPAC name
L-Tyrosyl-L-prolyl-L-glutaminyl-L-prolyl-L-glutaminyl-L-prolyl-L-phenylalanine
Other names
Gluteomorphin; Gliadorphin-7
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C43H57N9O11/c44-28(23-26-12-14-27(53)15-13-26)40(59)50-20-4-9-32(50)37(56)47-29(16-18-35(45)54)41(60)51-21-5-10-33(51)38(57)48-30(17-19-36(46)55)42(61)52-22-6-11-34(52)39(58)49-31(43(62)63)24-25-7-2-1-3-8-25/h1-3,7-8,12-15,28-34,53H,4-6,9-11,16-24,44H2,(H2,45,54)(H2,46,55)(H,47,56)(H,48,57)(H,49,58)(H,62,63)/t28-,29-,30-,31-,32-,33-,34-/m0/s1
    Key: QGFISQMZJLWFEE-NXBWRCJVSA-N
  • InChI=1/C43H57N9O11/c44-28(23-26-12-14-27(53)15-13-26)40(59)50-20-4-9-32(50)37(56)47-29(16-18-35(45)54)41(60)51-21-5-10-33(51)38(57)48-30(17-19-36(46)55)42(61)52-22-6-11-34(52)39(58)49-31(43(62)63)24-25-7-2-1-3-8-25/h1-3,7-8,12-15,28-34,53H,4-6,9-11,16-24,44H2,(H2,45,54)(H2,46,55)(H,47,56)(H,48,57)(H,49,58)(H,62,63)/t28-,29-,30-,31-,32-,33-,34-/m0/s1
    Key: QGFISQMZJLWFEE-NXBWRCJVBL
  • c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]4CCCN4C(=O)[C@H](Cc5ccc(cc5)O)N
Properties
C43H57N9O11
Molar mass 875.981 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gliadorphin (also known as gluteomorphin) is an opioid peptide that is formed during digestion of the gliadin component of the gluten protein. It is usually broken down into amino acids by digestion enzymes. It has been hypothesized that children with autism have abnormal leakage from the gut of this compound. This is partly the basis for the gluten-free, casein-free diet. Abnormally high levels of gliadorphin have been found in the urine of autistic children via mass spectrometry testing.[1]

References

  1. ^ Christison GW, Ivany K (2006). "Elimination diets in autism spectrum disorders: any wheat amidst the chaff?". J Dev Behav Pediatr. 27 (2 Suppl 2): S162–71. doi:10.1097/00004703-200604002-00015. PMID 16685183.


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