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Merck

76157

(4R)-4-Hydroxy-L-glutamic acid

≥98.0% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H9NO5
CAS Number:
2485-33-8
Molecular Weight:
163.13
NACRES:
NA.28
PubChem Substance ID:
329766558
UNSPSC Code:
12352202
MDL number:
MFCD00672375
Beilstein/REAXYS Number:
1725871

Key Documents

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Product Name

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

InChI key

HBDWQSHEVMSFGY-STHAYSLISA-N

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

assay

≥98.0% (TLC)

form

powder

optical activity

[α]/D 20.5±1.5°, c = 1 in H2O

color

white

mp

171 °C

storage temp.

−20°C

Quality Level

100

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1 of 4

This Item
C4375G3640G1135
(4R)-4-Hydroxy-L-glutamic acid ≥98.0% (TLC)

Sigma-Aldrich

76157

(4R)-4-Hydroxy-L-glutamic acid

N-Carbamyl-L-glutamic acid

Sigma-Aldrich

C4375

N-Carbamyl-L-glutamic acid

Glu-Glu

Sigma-Aldrich

G3640

Glu-Glu

L-Glutamic acid γ-(4-nitroanilide) γ-glutamyl transpeptidase substrate

Sigma-Aldrich

G1135

L-Glutamic acid γ-(4-nitroanilide)

form

powder

form

powder

form

powder

form

powder

assay

≥98.0% (TLC)

assay

≥98.0% (TLC)

assay

≥98% (TLC)

assay

≥98% (HPLC)

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

mp

171 °C

mp

-

mp

-

mp

-

color

white

color

white

color

white

color

-

Biochem/physiol Actions

(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. [1]
Substrate for aminotransferase[2]; pharmacological characterization at human glutamate transporter subtypes 1-3[3]; for studying structure-activity relationships (SAR) for ionotropic and metabotropic glutamate receptors[4].

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9072
BCCG4127
BCCB0435
BCBK2139V
BCBC1876V

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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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