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4-Hydroxyphenylglycine
| Column 1 | Column 2 |
|---|---|
| 4-Hydroxyphenylglycine (HPG). (R)-D-HPG shown on left; (S)-L-HPG shown on right. | |
| IUPAC name | |
| Nortyrosine | |
| Systematic IUPAC name | |
| Amino(4-hydroxyphenyl)acetic acid | |
| Other names | |
| 3-Amino-2,3,6-trideoxy-3-methyl-L-lyxo-hexopyranose | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}37784-25-1 |
| 3D model (JSmol) | Interactive image |
| Beilstein Reference | 513130 |
| ChEBI | CHEBI:50418CHEBI:15695 D |
| ChEMBL | ChEMBL130865 |
| ChemSpider | 83189 |
| ECHA InfoCard | 100.012.139 |
| EC Number | 213-353-2 |
| KEGG | C03493 D |
| PubChem CID | 92143 |
| UNII | 7UYG7X0F53 |
| CompTox Dashboard (EPA) | DTXSID90860473 |
| InChI | |
| Key: LJCWONGJFPCTTL-UHFFFAOYSA-N | |
| SMILES | |
| C1=CC(=CC=C1C(C(=O)O)N)O | |
| Chemical formula | C8H9NO3 |
| Molar mass | 167.164 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 | |
4-Hydroxyphenylglycine (HPG) is a non-proteogenic amino acid found in vancomycin and related glycopeptides. HPG is synthesized from the shikimic acid pathway and requires four enzymes to synthesize: Both L- and D-HPG are used in the vancomycin class of antibiotics. Tyrosine, a similar amino acid, differs by a methylene group (CH2) between the aromatic ring and the alpha carbon.
Biosynthesis of HPG
HPG is synthesized from prephenate, an intermediate in the shikimic acid pathway and also a precursor to tyrosine. Prephenate is aromatized by prephenate dehydrogenase (Pdh) using NAD+ as a cofactor to produce 4-hydroxyphenylpyruvate. 4-Hydroxyphenylpyruvate is then oxidized by 4-hydroxymandelate synthase (4HmaS) using oxygen to form 4-hydroxymandelate and hydrogen peroxide. 4HmaS is a non-heme iron-dependent dioxygenase. The reaction mechanism of this unique oxidation was proposed by Choroba et al in 2000
Proposed mechanism by Choroba et al for the oxidation of 4-hydroxymandelate.
4-Hydroxymandelate is subsequently oxidized by hydroxymandelate oxidase (Hmo) to 4-hydroxylbenzoylformate, using FMN as a cofactor. Finally, 4-hydroxyphenylglycine transaminase (HpgT) transfers an ammonia moiety from a donor to 4-hydroxylbenzoylformate to form HPG. Several different molecules can serve as the nitrogen donor for the transamination, however, Hubbard et al suspect L-tyrosine to serve as the most efficient donor. By doing so, the following cycle is constructed:
HPG synthetic cycle
HPG is also synthesized in Herpetosiphon aurantiacus using enzymes Haur_(1871,1887,1888).
- Vancomycin
- Oritavancin
- Glycopeptide antibiotics
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