Gliadorphin

Gliadorphin

Names
IUPAC name L-Tyrosyl-L-prolyl-D-glutaminyl-L-prolyl-L-glutaminyl-D-prolyl-D-phenylalanine
Other names Gluteomorphin; Gliadorphin-7
Identifiers
CAS Number	107936-65-2
ChemSpider	26567452
Jmol interactive 3D	Image
InChI 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-HMJDZOACSA-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-HMJDZOACBP
SMILES 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
Chemical formula	C43H57N9O11
Molar mass	875.98 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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, which then passes into the brain and disrupts brain function. This is partly the basis for the gluten-free, casein-free diet. Studies of this diet have had important methodological flaws, and the scientific evidence is not adequate to make treatment recommendations. However, abnormally high levels of gliadorphine 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.