Dihydroxyphenylglycine

For the antiviral drug, see ganciclovir.
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)
ChemSpider
MeSH 3,5-dihydroxyphenylglycine
UNII
  • 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) checkY
    Key: RCPPFACRJDEDFY-UHFFFAOYSA-N checkY
  • 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
  • C1=CC(=C(C=C1[C@@H](C(=O)O)N)O)O
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).
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(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.

  1. ^ 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.
  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.