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Sigma-Aldrich

(4R)-4-Hydroxy-L-glutaminsäure

≥98.0% (TLC)

Synonym(e):

erythro-(4R)-4-Hydroxy-L-glutaminsäure, H-(2S,4R)-γ-Hydroxy-Glu-OH

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About This Item

Empirische Formel (Hill-System):
C5H9NO5
CAS-Nummer:
2485-33-8
Molekulargewicht:
163.13
Beilstein:
1725871
MDL-Nummer:
MFCD00672375
UNSPSC-Code:
12352202
PubChem Substanz-ID:
329766558
NACRES:
NA.28

product name

(4R)-4-Hydroxy-L-glutaminsäure, ≥98.0% (TLC)

Assay

≥98.0% (TLC)

Form

powder

Optische Aktivität

[α]/D 20.5±1.5°, c = 1 in H2O

Farbe

white

mp (Schmelzpunkt)

171 °C

Lagertemp.

−20°C

SMILES String

N[C@@H](C[C@@H](O)C(O)=O)C(O)=O

InChI

1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)/t2-,3+/m0/s1

InChIKey

HBDWQSHEVMSFGY-STHAYSLISA-N

Biochem./physiol. Wirkung

(4R)-4-Hydroxy-L-glutamic acid or (2S,4R)-4-hydroxyglutamate was shown to activate the metabotropic glutamate receptors, mGlu1a, mGlu2, and mGlu8a in a dose-dependent manner.
Substrate for aminotransferase; pharmacological characterization at human glutamate transporter subtypes 1-3; for studying structure-activity relationships (SAR) for ionotropic and metabotropic glutamate receptors.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Metabolism of gamma-hydroxyglutamic acid. I. Conversion to alpha-hydroxy-gamma-ketoglutarate by purified glutamic-aspartic transaminase to rat liver.
A GOLDSTONE et al.
The Journal of biological chemistry, 237, 3476-3485 (1962-11-01)
Lennart Bunch et al.
ChemMedChem, 4(11), 1925-1929 (2009-09-05)
Subtype-selective ligands are of great interest to the scientific community, as they provide a tool for investigating the function of one receptor or transporter subtype when functioning in its native environment. Several 4-substituted (S)-glutamate (Glu) analogues were synthesized, and altogether
A S Bessis et al.
Bioorganic & medicinal chemistry letters, 11(12), 1569-1572 (2001-06-20)
The (2S,4R)- and (2S,4S)-4-hydroxyglutamates activate cloned mGlu(1a), mGlu(2), and mGlu(8a) receptors with different potencies. Best results were obtained with the (2S,4S) isomer being almost as potent as glutamate on mGlu(1a)R and mGlu(8a)R. Data are interpreted on the basis of the
Sebastien Alaux et al.
Journal of medicinal chemistry, 48(25), 7980-7992 (2005-12-13)
A series of nine L-2,4-syn-4-alkylglutamic acid analogues (1a-i) were synthesized in high yield and high enantiomeric excess (>99% ee) from their corresponding 4-substituted ketoglutaric acids (2a-i), using the enzyme aspartate aminotransferase (AAT) from pig heart or E. coli. The synthesized

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