Dihydroxyphenylglycine

Dihydroxyphenylglycine
Names
	IUPAC name (S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid
	Other names 3,5-dihydroxyphenylglycine, DHPG, S-DHPG
Identifiers
CAS Number	162870-29-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	11377133 ;
MeSH	3,5-dihydroxyphenylglycine
PubChem CID	443586;
UNII	CF5G2G268A ;
CompTox Dashboard (EPA)	DTXSID901311536 ;
	InChI InChI=1S/C8H9NO4/c10-6-3-1-2-5(8(6)13)9-4-7(11)12/h1-3,9-10,13H,4H2,(H,11,12) Key: RCPPFACRJDEDFY-UHFFFAOYSA-N ; InChI=1/C8H9NO4/c10-6-3-1-2-5(8(6)13)9-4-7(11)12/h1-3,9-10,13H,4H2,(H,11,12) Key: RCPPFACRJDEDFY-UHFFFAOYAU;
	SMILES C1=CC(=C(C=C1[C@@H](C(=O)O)N)O)O;
Properties
Chemical formula	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). verify (what is ?) 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.^[1] Agonist activity is found in only the (S)-isomer, and (S)-DHPG may be a partial agonist of group I mGluRs.^[1]

(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.^[1]

3,5-Dihydroxyphenylglycine can be isolated from the latex of Euphorbia helioscopia.^[2]

DHGP is also found in vancomycin and related glycopeptides. Although the (S) stereoisomer is synthesized by the DpgA-D enzymes,^[3] it is the (R) stereoisomer that is used in vancomycin and other related compounds. DHPG is enzymatically derived from the polyketide synthase pathway.

^ ^a ^b ^c Wiśniewski K.; Car, H. (2002). "(S)-3,5-DHPG: a review". CNS Drug Rev. 8 (1): 101–116. doi:10.1111/j.1527-3458.2002.tb00218.x. PMC 6741645. PMID 12070529.
^ Müller, P.; Schütte, H. R. (May 1968). "m-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine, 2 new amino acids from the latex of Euphorbia helioscopia". Z. Naturforsch. B (in German). 23 (5): 659–663. doi:10.1515/znb-1968-0516. PMID 4385921. S2CID 94822221.
^ Yim, G., Thaker, M. N., Koteva, K., Wright, G. "Glycopeptide antibiotic biosynthesis." The Journal of Antibiotics, 2017, 67, 31-41.

[CNSreview-1] Wiśniewski K.; Car, H. (2002). "(S)-3,5-DHPG: a review". CNS Drug Rev. 8 (1): 101–116. doi:10.1111/j.1527-3458.2002.tb00218.x. PMC 6741645. PMID 12070529.

[2] Müller, P.; Schütte, H. R. (May 1968). "m-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine, 2 new amino acids from the latex of Euphorbia helioscopia". Z. Naturforsch. B (in German). 23 (5): 659–663. doi:10.1515/znb-1968-0516. PMID 4385921. S2CID 94822221.

[3] Yim, G., Thaker, M. N., Koteva, K., Wright, G. "Glycopeptide antibiotic biosynthesis." The Journal of Antibiotics, 2017, 67, 31-41.

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