128052-92-6

Basic information

• Product Name: (1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride
• Synonyms: (+)-(1S,2R)-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID HYDROCHLORIDE;(1S,2R)-(+)-2-AMINO-1-CYCLOPENTANECARBOXYLIC ACID HYDROCHLORIDE;(1S,2R)-CISPENTACIN HYDROCHLORIDE;(1S,2R)-2-amino cyclopetanecarboxylic acid hydrochloride;(1S,2R)-2-amino cyclopetanecarboxylic acid hydrochloride salt;(1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylicacidHCl;(1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylicacid hydrochloride,98%;(1S,2R)-2-aminocyclopentanecarboxylic acid hydrochloride
• CAS NO: 128052-92-6
• Molecular Formula: C6H12ClNO2
• Molecular Weight: 165.62
• Mol File: 128052-92-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 162-166 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• Appearance: Off-white/Powder
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: soluble
• CAS DataBase Reference: (1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(128052-92-6)
• EPA Substance Registry System: (1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(128052-92-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 128052-92-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C6H11NO2.ClH/c7-5-3-1-2-4(5)6(8)9;/h4-5H,1-3,7H2,(H,8,9);1H/t4-,5+;/m0./s1

Upstream product

• 122672-46-2 (-)-cispentacin 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 359586-68-8 (1S,2S)-2-[(1'S)-phenylethyl]aminocyclopentanecarboxylic acid 
• 1609100-30-2 ethyl cis-2-aminocyclopentane-1-carboxylate 
• 197916-36-2 ethyl (1R,2S)-2-aminocyclopentane-1-carboxylate 
• 1039114-07-2 (1R,2S)-2-Isocyanato-cyclopentanecarboxylic acid methyl ester 
• 142-29-0 cyclopentene 
• 39155-95-8 (1S,5R)-6-azabicyclo<3.2.0>heptan-7-one 
• 179123-04-7 N-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 22031-52-3 2-aza-3-oxobicyclo<3.2.0>heptane 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 179462-33-0 (1S,5R)-6-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 158414-41-6 (1S,2R,αR)-tert-butyl 2-(N-benzyl-N-α-methylbenzylamino)cyclopentanecarboxylate 
• 87661-18-5 1,1-dimethylethyl cyclopentanecarboxylate 

Downstream Products

• 862287-27-2 (1S,2S)-2-aminocyclopentanecarboxylic acid methyl ester 
• 1203556-26-6 (1S,2R)-Fmoc-2-amino-1-cyclopentanecarboxylic acid 
• 282524-97-4 Fmoc-cis-2-amino-1-cyclopentanecarboxylic acid 
• 282524-97-4 rel-(1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid 
• 1033756-03-4 (1R,2S)-2-(4-fluoro-benzylamino)-cyclopentanecarboxylic acid methyl ester 
• 154460-33-0 (1R,2S)-2-amino-cyclopentanecarboxylic acid methyl ester 
• 362485-20-9 methyl (1S,2R)-2-aminocyclopentane-1-carboxylate 
• 135053-11-1 trans-2-aminocyclopentanecarboxamide 
• 135053-11-1 cis-2-amino-1-cyclopentanecarboxamide 
• 359586-64-4 (1S,2S)-2-(9H-fluoren-9-ylmethoxycarbonyl)amino-cyclopentanecarboxylic acid 
• 359586-69-9 (1R,2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopentanecarboxylic acid 

Relevant articles and documents

Biocatalysis for the preparation of optically active β-lactam precursors of amino acids

Enantioselective acylation of N-hydroxymethylated β-lactams in the presence of Pseudomonas sp. lipase afforded optically active precursors for the preparation of (1R,2S)- and (1S,2R)-2-aminocyclopentane- and (1R,2S,3R,4S)- and (1S,2R,3S,4R)-3-aminobicyclo[2.2.1]heptanecarboxylic acids. Due to the high enantioselectivity (E = 90 and 62) and in order to minimize the enzymatic hydrolysis of the acylated products back to the starting alcohol, the reactions were performed in acetone.

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.

New compounds

The present invention encompasses compounds of general formula (1) wherein R1, R2, R4, X, m, n and p are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.