Indolyl-3-acryloylglycine

Indolyl-3-acryloylglycine, also known as trans-indolyl-3-acryloylglycine, or IAG for short, is a compound consisting of an indole group attached to an acrylic acid moiety, which is in turn attached to a glycine molecule. This compound has been shown to isomerize when exposed to light.[1] It is likely a metabolic intermediate in the biosynthesis of tryptophan,[2] and is synthesized from tryptophan via indolepropionic acid and indoleacrylicacid (IAcrA). It is also likely that IAcrA is converted into IAG in the gut wall.[3] It may also be produced by certain elements of the mammalian gut microbiota by phenylalanine ammonia-lyase.[4] Identifiable in the urine by high-performance liquid chromatography, it may be a biomarker for autism spectrum disorders, as demonstrated by the research of Paul Shattock[5][6][7] and other researchers from Australia.[8] These researchers have reported that urinary levels of IAG are much higher in autistic children than in controls; however, other researchers have found no association between IAG concentrations in the urine and autism.[9] Its excretion in the urine may also be changed in Hartnup disease and celiac disease,[10] as well as photodermatosis, muscular dystrophy, and liver cirrhosis.[11]

Indolyl-3-acryloylglycine
Names
IUPAC name
2-[[(''E'')-3-(1H-indol-3-yl)prop-2-enoyl]amino]acetic acid
Other names
indoleacrylic glycine
Identifiers
3D model (JSmol)
Properties
C13H12N2O3
Molar mass 244.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Mills, M. J.; Savery, D.; Shattock, P. E. (1998). "Rapid analysis of low levels of indolyl-3-acryloylglycine in human urine by high-performance liquid chromatography". Journal of Chromatography B. 712 (1–2): 51–58. doi:10.1016/S0378-4347(98)00153-4. PMID 9698228.
  2. Marklová, E. (1999). "Where does indolylacrylic acid come from". Amino Acids. 17 (4): 401–413. doi:10.1007/BF01361665. PMID 10707769.
  3. Shattock, Paul. "The Role of Tryptophan in Autism and Related Disorders" (PDF). The Nutrition Practitioner (Summer 2006).
  4. Clayton, T. A. (2012). "Metabolic differences underlying two distinct rat urinary phenotypes, a suggested role for gut microbial metabolism of phenylalanine and a possible connection to autism". FEBS Letters. 586 (7): 956–961. doi:10.1016/j.febslet.2012.01.049. PMID 22306194.
  5. Anderson, R. J.; Bendell, D. J.; Garnett, I.; Groundwater, P. W.; Lough, W. J.; Mills, M. J.; Savery, D.; Shattock, P. E. G. (2002). "Identification of indolyl-3-acryloylglycine in the urine of people with autism". Journal of Pharmacy and Pharmacology. 54 (2): 295–298. doi:10.1211/0022357021778349. PMID 11858215.
  6. Bull, G.; Shattock, P.; Whiteley, P.; Anderson, R.; Groundwater, P. W.; Lough, J. W.; Lees, G. (2003). "Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders". Medical science monitor : international medical journal of experimental and clinical research. 9 (10): CR422–CR425. PMID 14523330.
  7. Whiteley, P.; Mrpharms, P. S. (2003). "What Makes Trans‐indolyl‐3‐acryloylglycine Identified by High‐performance Liquid Chromatography Relevant to Pervasive Developmental Disorders?". Journal of Nutritional and Environmental Medicine. 13 (4): 231. doi:10.1080/13590840310001641996.
  8. Wang, L.; Angley, M. T.; Gerber, J. P.; Young, R. L.; Abarno, D. V.; McKinnon, R. A.; Sorich, M. J. (2009). "Is urinary indolyl-3-acryloylglycine a biomarker for autism with gastrointestinal symptoms?". Biomarkers. 14 (8): 596–603. doi:10.3109/13547500903183962. PMID 19697973.
  9. Wright, B.; Brzozowski, A. M.; Calvert, E.; Farnworth, H.; Goodall, D. M.; Holbrook, I.; Imrie, G.; Jordan, J.; Kelly, A.; Miles, J.; Smith, R.; Town, J. (2005). "Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder?". Developmental Medicine & Child Neurology. 47 (3): 190–192. doi:10.1017/S0012162205000344. PMID 15739724.
  10. Keszthelyi, D.; Troost, F. J.; Masclee, A. A. M. (2009). "Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function". Neurogastroenterology & Motility. 21 (12): 1239. doi:10.1111/j.1365-2982.2009.01370.x. PMID 19650771.
  11. Marklová, E.; Fojtásková, A. (1996). "High-performance liquid chromatographic profiling of indolylacryloylglycine and its possible precursors in body fluids". Journal of Chromatography A. 730 (1–2): 133–137. doi:10.1016/0021-9673(95)00943-4. PMID 8680585.


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