64769-66-0

Basic information

• Product Name: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID
• Synonyms: L-TRANS-4-CARBOXY-L-PROLINE;L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID;L-TRANS-2,4-PDC;TRANS-4-CARBOXY-L-PROLINE;2,4-Pyrrolidinedicarboxylicacid,(2S,4R)-(9CI);Zinc03796127;(2S,4R)-pyrrolidine-2,4-dicarboxylic acid
• CAS NO: 64769-66-0
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.14
• Product Categories: PYRROLE;Glutamate receptor
• Mol File: 64769-66-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 355.3 °C at 760 mmHg
• Flash Point: 168.7 °C
• Appearance: /
• Density: 1.456 g/cm³
• Vapor Pressure: 5.28E-06mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Store at RT
• Solubility: Water (Slightly)
• CAS DataBase Reference: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(64769-66-0)
• EPA Substance Registry System: L-TRANS-PYRROLIDINE-2,4-DICARBOXYLIC ACID(64769-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 64769-66-0(Hazardous Substances Data)

Usage

Uses

L-trans-Pyrrolidine-2,4-dicarboxylic Acid is an inhibitor of the glutamate transporter EAAT.

Biological Activity

Potent, competitive, transportable EAAT1-4 inhibitor/non-transportable EAAT5 inhibitor. Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset? .

InChI:InChI=1/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

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 135999-86-9 2-Acetylamino-2,4-bis-ethoxycarbonyl-4-(toluene-4-sulfonyloxymethyl)-pentanedioic acid diethyl ester 
• 135999-85-8 tetraethyl 1-acetamido-4-hydroxybutane-1,1,3,3-tetracarboxylate 
• 188345-72-4 2,2,2-trichloroethyl (+/-)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 188345-71-3 2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene 
• 139927-14-3 (+/-)-2-benzoyl-2-azabicyclo<2.2.1>hept-5-ene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 6671-85-8 2-azabicyclo[2.2.1]hept-5-ene 
• 130830-61-4 N-(benzyloxycarbonyl)-cis-4-(tosyloxy)-L-proline ethyl ester 
• 130830-70-5 N-(benzyloxycarbonyl)-trans-4-carboxy-L-proline dimethyl ester 
• 130830-66-9 N-(benzyloxycarbonyl)-trans-4-cyano-L-proline ethyl ester 

Relevant articles and documents

Asymmetric synthesis of 2,4-disubstituted pyrrolidines

A new strategy for asymmetric synthesis of 2,4-disubstituted pyrrolidines is described, starting from readily available chiral building blocks 1 and (2R)-2,3-O-isopropylideneglycealdehyde (6).

Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.

Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer

In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.