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

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

• 130830-74-9 N-(benzyloxycarbonyl)-trans-4-carboxy-L-proline 
• 64750-03-4 (2S,4R)-4-methoxycarbonylproline methyl ester 
• 220047-57-4 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 
• 212266-75-6 (2S,4R)-1-tert-butoxycarbonyl-2-hydroxymethyl-4-hydroxymethylpyrrolidine 
• 212266-76-7 1-(tert-butyl) 2,4-dimethyl (2S,4R)-pyrrolidine-1,2,4-tricarboxylate 
• 212266-74-5 (2R,4R)-3-Benzenesulfonyl-2,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220047-97-2 (2R,3S,4R)-3-Benzenesulfonyl-2,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 212266-72-3 ((3R,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol 
• 220047-66-5 ((3R,4S,5R)-4-Benzenesulfonyl-1-benzyl-5-benzyloxymethyl-pyrrolidin-3-yl)-methanol 
• 212266-71-2 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-(S)-1-oxiranylmethyl-amine 
• 212266-69-8 (S)-3-[((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-amino]-propane-1,2-diol 
• 212266-68-7 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 
• 130930-26-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl 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).

Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

Treatment of readily available chiral building block 1 with (2R)-2,3-O- isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline- glutamic acid, are synthesized in highly diastereomerically pure forms.

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.

An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral imidazolinium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g. naturally occurring proline derivatives and homochiral pyrrolizidines.

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.

Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids

The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis