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P7575

Sigma-Aldrich

L-trans-Pyrrolidine-2,4-dicarboxylic acid

≥98%

Synonym(s):

(2S,4R)-Pyrrolidine-2,4-Dicarboxylic Acid, L-trans-2,4-PDC, trans-4-Carboxy-L-proline

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About This Item

Empirical Formula (Hill Notation):
C6H9NO4
CAS Number:
64769-66-0
Molecular Weight:
159.14
MDL number:
MFCD00153866
UNSPSC Code:
12352106
PubChem Substance ID:
24898859
NACRES:
NA.77

Assay

≥98%

form

powder

SMILES string

OC(=O)[C@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C6H9NO4/c8-5(9)3-1-4(6(10)11)7-2-3/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4+/m1/s1

InChI key

NRSBQSJHFYZIPH-DMTCNVIQSA-N

Gene Information

rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409) , Slc1a2(29482) , Slc1a3(29483)

Application

L-trans-Pyrrolidine-2,4-dicarboxylic acid has been used:
  • as a glutamate transport inhibitor to test its impairing effect on glutamate-induced cell death in HT22 neuronal cells
  • as an analog of glutamate to test its effect on glutamate/glutamine-dependent acid resistance of E. coli and S. flexneri
  • as sodium glutamate (Na+/Glu) cotransporter inhibitor in myogenic cell line C2C12

Biochem/physiol Actions

L-trans-Pyrrolidine-2,4-dicarboxylic acid is a selective glutamate transporter inhibitor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jan Lewerenz et al.
Journal of neurochemistry, 98(3), 916-925 (2006-06-15)
Oxidative glutamate toxicity in the neuronal cell line HT22 is a model for cell death by oxidative stress. In this paradigm, an excess of extracellular glutamate blocks the glutamate/cystine-antiporter system Xc-, depleting the cell of cysteine, a building block of
Imane Nafia et al.
Journal of neurochemistry, 105(2), 484-496 (2007-11-29)
Nigral depletion of the main brain antioxidant GSH is the earliest biochemical event involved in Parkinson's disease pathogenesis. Its causes are completely unknown but increasing number of evidence suggests that glutamate transporters [excitatory amino acid transporters (EAATs)] are the main
Yingmei Zhang et al.
CNS neuroscience & therapeutics, 30(1), e14487-e14487 (2023-10-07)
Chronic cerebral hypoperfusion-induced demyelination causes progressive white matter injury, although the pathogenic pathways are unknown. The Single Cell Portal and PanglaoDB databases were used to analyze single-cell RNA sequencing experiments to determine the pattern of EAAT3 expression in CNS cells.
H-R Weng et al.
Neuroscience, 138(4), 1351-1360 (2006-01-24)
Glutamate is a primary excitatory neurotransmitter in the mammalian CNS. Glutamate released from presynaptic neurons is cleared from the synaptic cleft passively by diffusion and actively by glutamate transporters. In this study, the role of glutamate transporters in sensory processing
V J Balcar
FEBS letters, 300(3), 203-207 (1992-04-06)
Uptake of 1 microM [3H]L-glutamate by cultured 3T3 fibroblasts was strongly dependent on extracellular Na+; it was reduced by elevated concentrations of K+ (60 mM) but it was not influenced by variations in the concentration of Ca2+ (0-9.6 mM). D-
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