111900-32-4

Usage

Biological Activity

Active isomer of (±)-trans-ACPD ((?-1-Aminocyclopentane-trans-1,3-dicarboxylic acid ). Agonist at both group I and II mGlu receptors (EC 50 values are 5, 15, 42 and 60 μ M at mGluR 2 , mGluR 5 , mGluR 1 and mGluR 6 respectively).

InChI:InChI=1/C7H11NO4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4H,1-3,8H2,(H,9,10)(H,11,12)/t4-,7+/m1/s1

Upstream product

• 98-78-2 3-Oxo-cyclopentanecarboxylic acid 
• 112896-82-9 (5R,7R)-2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7-carboxylic acid 
• 112896-82-9 (5R,7S)-2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7-carboxylic acid 
• 190510-45-3 (S)-3-Cyano-1-ethoxycarbonylamino-cyclopentanecarboxylic acid ethyl ester 
• 444809-79-4 tert-butyl (5S,7R)-7-hydroxymethyl-2,2-dimethyl-1-aza-3-oxaspiro[4.4]nonane-1-carboxylate 
• 444809-80-7 (1S,3R)-(3-acetoxymethyl-1-acetylaminocyclopentyl)methyl acetate 
• 444809-78-3 tert-butyl (S)-7-hydroxymethyl-2,2-dimethyl-1-aza-3-oxaspiro[4.4]non-6-ene-1-carboxylate 
• 444809-81-8 N-[(1S,3R)-1,3-bis(hydroxymethyl)cyclopentyl]acetamide 
• 475681-49-3 (4S)-2,2-dimethyl-7-(tert-butyldimethylsilanyloxymethyl)-1-oxa-3-azaspiro[4.4]non-6-ene-3-carboxylic acid tert-butyl ester 
• 444809-82-9 dimethyl (1S,3R)-1-acetylaminocyclopentane-1,3-dicarboxylate 
• 190510-46-4 (1S,3R)-1-Ethoxycarbonylamino-cyclopentane-1,3-dicarboxylic acid 
• 39026-63-6 trans-1-aminocyclopentane-1,3-dicarboxylic acid 
• 111900-31-3 (1S,3S)-ACPD 
• 122689-82-1 (1S)-isopropyl 3-oxocyclopentane-1-carboxylate 

Downstream Products

• 111900-32-4 (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid 
• 89253-38-3 (1R,3S)-ACPD 
• 111900-33-5 (1R,3R)-ACPD 
• 111900-31-3 (1S,3S)-ACPD 

Relevant academic research and scientific papers

Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.

Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid

An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.

Carbamate-directed hydroboration: Enantioselective synthesis of the excitatory amino acid 1-aminocyclopentane-1,3-dicarboxylic acid

Carbamate-directed hydroboration (using BH3) of 1-substituted 3- cyclopentenes 2, 6 and 9 and an enantioselective synthesis of the excitatory amine acid 1-aminocyclopentane-1,3-dicarboxylic acid via carbamate-directed asymmetric hydroboration [90% de, 45% ee using (+)-IpcBH2] of cyclopentene 2 are described.

Stereospecific synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid, a selective agonist of metabotropic glutamate receptors

(1S,3R)-Aminocyclopentane-1,3-dicarboxylic acid 1, a widely used metabotropic glutamate receptor agonist has been synthesized. Hydrolysis followed by Curtius rearrangement of 5 derived from dimethyl (S)-malate gave 6 with excellent diastereofacial selecti

Resolution and regioselective protection of glutamic acid analogues. I- Resolution of diastereomeric α-boroxazolidone derivatives

Diastereomeric α-boroxazolidone γ-phenylethylamide (or γ-phenylethanolamide) derivatives of 2-, 3- or 4-substituted glutamic acid analogues have been separated by silicagel chromatography, resulting, after deprotection, in a practical method for the resolution of most of these unnatural amino acids.

CHEMOENZYMATIC SYNTHESIS OF CONFORMATIONALLY RIGID GLUTAMIC ACID ANALOGUES

All stereomers of cyclohexane cyclopentane-derived analogues of glutamic acid have been synthesized from the corresponding 3-keto-cycloalkyl carboxylic acid esters by a combination of microbial steps and standard chemical methods.