71830-08-5

Usage

Uses

Used in Pharmaceutical Industry:
(1R,3S)-3-Aminocyclopentanecarboxylic acid is used as a pharmaceutical intermediate for the synthesis of a wide range of medicinal compounds, contributing to the development of innovative treatments and therapies.
Used in Peptide Synthesis:
(1R,3S)-3-Aminocyclopentanecarboxylic acid is utilized in the synthesis of aminocyclopentanecarboxylic acid-containing cyclic RGD peptides, which have potential applications in various biomedical fields, such as drug delivery and targeting.
Used in CCR1 Antagonist Preparation:
(1R,3S)-3-Aminocyclopentanecarboxylic acid is employed in the preparation of BMS-457, a potent and selective CCR1 antagonist, which may have therapeutic applications in treating conditions related to chemokine receptor 1, such as inflammatory and autoimmune diseases.

InChI:InChI=1/C6H11NO2/c7-5-2-1-4(3-5)6(8)9/h4-5H,1-3,7H2,(H,8,9)/t4-,5+/m1/s1

Upstream product

• 876-05-1 cis-1,3-cyclopentanedicarboxylic acid 
• 714195-06-9 methyl 3-aminocyclopentane-1-carboxylate 
• 102579-71-5 cis-4-amino-cyclopent-2-ene-1-carboxylic acid 
• 74201-94-8 methyl 3-(N-benzyloxycarbonylamino)cyclopent-1-ene-1-carboxylate 
• 74201-88-0 3-aminocyclopent-1-ene-1-carboxylic acid 
• 74201-92-6 3-bromocyclopent-1-ene-1-carbonitrile 
• 3047-38-9 cyclopent-1-enecarbonitrile 
• 49805-27-8 3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 
• 96443-42-4 (+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid 

Downstream Products

• 220497-67-6 (1R,3S)-3-(9-fluorenylmethoxycarbonylamino)cyclopentanecarboxylic acid 
• 180323-49-3 (1S,3R)-3-amino-cyclopentanecarboxylic acid methyl ester hydrochloride 
• 1291779-96-8 (1R,3S)-3-propionylamino-cyclopentanecarboxylic acid N-methyl-N-(4-(1-methyl-1H-benzoimidazol-2-yl)-phenyl)-amide 
• 789468-94-6 methyl (1R,3S)-3-aminocyclopentane-1-carboxylate 
• 1311203-74-3 (1R,3S)-3-(4-cyanophenylamino)cyclopentanecarboxylic acid 
• 1311231-63-6 (1R,3S)-3-[4-{5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl}phenylamino]cyclopentanecarboxylic acid 
• 1332365-10-2 ethyl (1R,3S)-3-(4-cyanophenylamino)cyclopentanecarboxylate 
• 1312023-76-9 C₁₅H₂₁N₃O₃ 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1332365-13-5 ethyl (1R,3S)-3-[4-{5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl}phenylamino]cyclopentanecarboxylate 
• 1311203-75-4 (1R,3S)-3-(4-cyano-2-methyl-phenylamino)-cyclopentanecarboxylic acid 
• 1332365-11-3 (1R,3S)-ethyl 3-(2-bromo-4-cyanophenylamino)cyclopentanecarboxylate 
• 1311258-46-4 (1R,3S)-3-(4-cyano-2-methyl-phenylamino)-cyclopentanecarboxylic acid ethyl ester 
• 1311258-47-5 (1R,3S)-3-[4-(N'-hydroxycarbamimidoyl)-2-methyl-phenylamino]-cyclopentanecarboxylic acid ethyl ester 

Relevant academic research and scientific papers

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.

Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Enantioselective synthesis of (+) and (-)-cis-3-aminocyclopentanecarboxylic acids by enzymatic asymmetrization

Both enantiomers of cis-3-aminocyclopentanecarboxylic acid (GABA analogs, inhibitory neurotransmitter) have been prepared via enzymatic asymmetrization of cis -1,3-cyclopentanedicarboxylic acid.