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Names | |
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Preferred IUPAC name
[(2E)-3-(1H-Indol-3-yl)prop-2-enamido]acetic acid | |
Other names
indoleacrylic glycine
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Identifiers | |
3D model (
JSmol)
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PubChem
CID
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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).
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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]
![]() | |
Names | |
---|---|
Preferred IUPAC name
[(2E)-3-(1H-Indol-3-yl)prop-2-enamido]acetic acid | |
Other names
indoleacrylic glycine
| |
Identifiers | |
3D model (
JSmol)
|
|
PubChem
CID
|
|
| |
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).
|
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]