111900-31-3

Basic information

• Product Name: (1S,3R)-ACPD
• Synonyms: TRANS-(1S,3R)-1-AMINO-1,3-CYCLOPENTANEDICARBOXYLIC ACID;TRANS-(1S,3R)-ACPD;(1S,3S)-ACPD;(1S,3S)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID;(1S,3R)-ACPD;(1S,3R)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID;(1S)-1α-Amino-1,3α-cyclopentanedicarboxylic acid;(1S,3R)-1-Amino-1,3-cyclopentanedicarboxylic acid
• CAS NO: 111900-31-3
• Molecular Formula: C₇H₁₁NO₄
• Molecular Weight: 173.17
• Mol File: 111900-31-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 352.7±42.0 °C(Predicted)
• Appearance: white/solid
• Density: 1.452±0.06 g/cm3(Predicted)
• Solubility: ethanol: 0.24 mg/mL
• PKA: 2.11±0.40(Predicted)
• CAS DataBase Reference: (1S,3R)-ACPD(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R)-ACPD(111900-31-3)
• EPA Substance Registry System: (1S,3R)-ACPD(111900-31-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: GY4060000
• Hazardous Substances Data: 111900-31-3(Hazardous Substances Data)

Usage

Uses

trans-(1S,3R)-ACPD is a rigid glutamate analog and mGluR activator.

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 
• 122689-80-9 isopropyl 3-oxocyclopent-1-ene-1-carboxylate 
• 122689-81-0 (S)-3-Hydroxy-cyclopentanecarboxylic acid isopropyl ester 
• 108384-36-7 cyclopentene ⁽²⁾-1-one-3 methylcarboxylate 
• 55843-47-5 (S)-3-Hydroxy-cyclopentanecarboxylic acid 
• 71830-06-3 (-)-(S)-3-oxocyclopentanecarboxylic acid 
• 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 
• 39026-63-6 trans-(+/-)-1-amino-1,3-cyclopentanedicarboxylic acid 
• 151-50-8 potassium cyanide 
• 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 articles and documents

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.

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.

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.