122672-46-2

Usage

Uses

Used in Chemical Research:
(1R,2S)-2-Aminocyclopentanecarboxylic acid is used as a research compound for studying the properties and potential applications of non-proteinogenic amino acids. Its unique structure and stereochemistry make it an interesting subject for investigation in the field of organic chemistry.
Used in Biochemical Research:
In the field of biochemistry, (1R,2S)-2-Aminocyclopentanecarboxylic acid is employed as a tool to understand the interactions and functions of non-standard amino acids within biological systems. Its presence may provide insights into the role of such amino acids in various biochemical processes and their potential as therapeutic agents.
Used in Pharmaceutical Development:
(1R,2S)-2-Aminocyclopentanecarboxylic acid is used as a starting material or intermediate in the synthesis of novel pharmaceutical compounds. Its unique structural features may contribute to the development of new drugs with specific therapeutic properties, particularly in the area of amino acid-based therapeutics.
Used in Material Science:
In material science, (1R,2S)-2-Aminocyclopentanecarboxylic acid may be utilized in the design and synthesis of new materials with tailored properties. Its incorporation into polymers or other materials could lead to the development of advanced materials with applications in various industries, such as electronics, coatings, or biomedical devices.

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

Upstream product

• 39155-94-7 (1R,5S)-6-azabicyclo[3.2.0]heptan-7-one 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 35878-28-5 cyclopentane-cis-1,2-dicarboxylic acid anhydride 
• 152495-66-4 (E)-7-(1,3-dithian-2-yl)-3-hepten-2-one 
• 179123-04-7 N-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 142-29-0 cyclopentene 
• 22031-52-3 2-aza-3-oxobicyclo<3.2.0>heptane 
• 138127-85-2 (1R,5S)-6-azabicyclo<3.2.0>hept-3-en-7-one 
• 145213-16-7 (1S,2R)-1-(tert-butoxycarbonylamino)-2-<(1R^*,2R^*)-1,2-dihydroxypropyl>cyclopentane 
• 145213-15-6 (1S,4R,5R)-2-benzyl-4-<(R^*)-1-hydroxyethyl>-3-oxa-2-azabicyclo<3.3.0>octane 
• 145213-19-0 (R)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-ol 
• 145150-93-2 (+/-)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-ol 
• 145150-86-3 (R)-(E)-7-hydroxy-5-octenal 
• 145213-17-8 (+/-)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-yl acetate 

Downstream Products

• 282524-97-4 (1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid 
• 128052-92-6 (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid hydrochloride 
• 592503-69-0 cis-(1S,2R)-2-acetylamino-cyclopentanecarboxylic acid methyl ester 
• 1416585-19-7 C₁₂H₁₅NO₂ 
• 1416585-21-1 C₁₂H₁₃NO 
• 1416585-20-0 C₁₃H₁₇NO₂ 
• 154460-33-0 (1R,2S)-2-amino-cyclopentanecarboxylic acid methyl ester 
• 879122-96-0 (1R,2S)-2-((R)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-cyclopentanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Identification of the Amipurimycin Gene Cluster Yields Insight into the Biosynthesis of C9 Sugar Nucleoside Antibiotics

Feeding studies indicate a possible synthetic pattern for the N-terminal cis-aminocyclopentane carboxylic acid (ACPC) and suggest an unusual source of the high-carbon sugar skeleton of amipurimycin (APM). The biosynthetic gene cluster of APM was identified and confirmed by in vivo experiments. A C9 core intermediate was discovered from null mutants of ACPC pathway, and an ATP-grasp enzyme (ApmA8) was reconstituted in vitro for ACPC loading. Our observations allow a first proposal of the APM biosynthetic pathway.

Chemoenzymatic synthesis of both enantiomers of cispentacin

Based on the lipase-catalysed kinetic resolution of the silyloxyalcohol (1RS,2SR)-5 by transesterification with vinyl acetate in the presence of lipase from Pseudomonas cepacia a synthesis of both enantiomers of the β-amino acid cispentacin (1R,2S)-1 and (1S,2R)-1 using simple functional group interconversions is described.

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

CYCLOALKYL-FUSED TETRAHYDROQUINOLINES AS CRTH2 RECEPTOR MODULATORS

The invention provides certain cycloalkyl-fused tetrahydroquinolines of the Formula (I), and their pharmaceutically acceptable salts and esters, wherein R1, R2, R7, R8, R8a, E, Y, Z, n, u, and t are a

Hairpin folding behavior of mixed α/β-peptides in aqueous solution

The invention of new strategies for the design of protein-mimetic oligomers that manifest the folding encoded in natural amino acid sequences is a significant challenge. In contrast to the α-helix, mimicry of protein β-sheets is less understood. We report

Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

(18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for favorable association. Enantiomeric discrimination of the two hydrogen atoms α to the amine and carboxylic acid moieties of the β-amino acid was observed with every substrate studied. Trends in the order of the enantiomeric discrimination of certain hydrogen atoms for substrates of similar structures correlate with the absolute configuration.

Vapour-assisted enzymatic hydrolysis of β-lactams in a solvent-free system

A new, solvent-free, vapour-assisted method, developed for the synthesis of carbocyclic cis β-amino acid enantiomers through the Candida antarctica lipase B-catalysed enantioselective (E >200) hydrolysis of β-lactams with 0.5 equiv of H2O at 70 °C, has been demonstrated to be applicable on a preparative scale to produce (±)-2 (the starting racemate for cispentacin), (±)-3 (the starting racemate for 4-tert-butylcispentacin, a new cispentacin analogue) and (±)-7 (the starting racemate for 1,4-ethylene-bridged cispentacin).

2,4-diamino-pyrimidines as aurora inhibitors

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.

Novel antifungal β-amino acids: Synthesis and activity against Candida albicans

A series of novel β-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. β-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections.

The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid.

Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.