Dihydroxyphenylglycine
| Names | |
|---|---|
| IUPAC name
(S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid | |
| Other names
3,5-dihydroxyphenylglycine, DHPG, S-DHPG | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| MeSH | 3,5-dihydroxyphenylglycine |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H9NO4 | |
| Molar mass | 183.05 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 | |
(S)-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.
DHPG was the first agonist shown to be selective for group I mGluRs. Agonist activity is found in only the (S)-isomer, and (S)-DHPG may be a partial agonist of group I mGluRs.
(S)-DHPG has been investigated for therapeutic effects in the treatment of neuronal injury (such as those associated with ischemia or hypoxia), cognitive enhancement, and Alzheimer's disease.
3,5-Dihydroxyphenylglycine can be isolated from the latex of Euphorbia helioscopia.
DHGP is also found in vancomycin and related glycopeptides. Although the (S) stereoisomer is synthesized by the DpgA-D enzymes, it is the (R) stereoisomer that is used in vancomycin and other related compounds. DHPG is enzymatically derived from the polyketide synthase pathway.