122672-46-2

Basic information

• Product Name: (1R,2S)-2-Aminocyclopentanecarboxylic acid
• Synonyms: Cyclopentanecarboxylic acid, 2-amino-, (1R,2S)- (9CI);(1R,2S)-2-AMINO-CYCLOPETANECARBOXYLIC ACID ;(1R,2S)-2-Aminocyclopentanecarboxylic acid;cis-2-Amino-1-cyclopentanecarboxylic acid;(1R)-2β-Amino-1β-cyclopentanecarboxylic acid;Antibiotic FR-109615;FR-109615;Cyclopentanecarboxylic acid, 2-aMino-, (1R-cis)-
• CAS NO: 122672-46-2
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: AMINOACID
• Mol File: 122672-46-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 264.7oC at 760 mmHg
• Flash Point: 113.9oC
• Appearance: /
• Density: 1.19g/cm3
• Vapor Pressure: 0.00278mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (1R,2S)-2-Aminocyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-Aminocyclopentanecarboxylic acid(122672-46-2)
• EPA Substance Registry System: (1R,2S)-2-Aminocyclopentanecarboxylic acid(122672-46-2)

Safety Data

• Hazardous Substances Data: 122672-46-2(Hazardous Substances Data)

Usage

General Description

"(1R,2S)-2-Aminocyclopentanecarboxylic acid is a chemical compound belonging to the class of organic compounds known as cyclohexylamines. Its systematic IUPAC name is (1R,2S)-2-amino-cyclopentanecarboxylic acid. As the name suggests, this particular compound contains a cyclopentane ring, which is a cyclic hydrocarbon with a five-membered ring, and a carboxylic acid group. Its specific stereoisomer configuration is indicated by the (1R,2S) prefix. It also involves an amino group (-NH2), contributing to its status as an amino acid, although it is not one of the 20 standard amino acids that make up proteins. Thus, (1R,2S)-2-Aminocyclopentanecarboxylic acid is most likely encountered in the exploration of non-proteinogenic amino acids in chemical or biochemical research.

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

• 179123-04-7 N-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 1026260-28-5 (1R,2S)-2-Azidocarbonyl-cyclopentanecarboxylic acid benzyl ester 
• 648433-16-3 (1S,2R)-cis-2-benzyloxycarbonyl-cyclopentane-1-carboxylic acid 
• 35878-28-5 cyclopentane-cis-1,2-dicarboxylic acid anhydride 
• 420124-09-0 (+)-(1R,2S)-N-benzyl-2-amino-cyclopentane-1 carboxylic acid 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 198022-68-3 (E)-Cinnamyl (1R,2S)-2-N-((E)-cinnamyloxycarbonyl)amino-cyclopentane-1-carboxylate 
• 186249-64-9 (1R,2S)-2-phthalimidocyclopentane-1-carboxylic acid 
• 158414-42-7 (1R,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester 
• 130981-12-3 (-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid 
• 136315-70-3 (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid 
• 39155-94-7 (1R,5S)-6-azabicyclo[3.2.0]heptan-7-one 
• 420124-05-6 (-)-2-(5,5-dimethoxy-pentylidene)-[1R,3R]-1,3-dioxo-1,3-dithiane 
• 420806-23-1 (+)-[1R,5S][1'R,3'R]-4-benzyl-1',3'-dioxo-4-aza-3-oxabicyclo[3.3.0]octane-2-spiro-2'-(1',3'-dithiane) 

Downstream Products

• 282524-97-4 (1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid 
• 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 
• 128052-92-6 (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid hydrochloride 

Relevant articles and documents

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.

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.

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