(1r,2s)-2-Aminocyclopentanecarboxylic acid

Base Information

• Chemical Name: (1r,2s)-2-Aminocyclopentanecarboxylic acid
• CAS No.: 122672-46-2
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• UNII: 9ZJP849D4I,Y1E02L9HC2
• DSSTox Substance ID: DTXSID40924231
• Nikkaji Number: J327.333D
• Wikidata: Q72435383
• ChEMBL ID: CHEMBL1191824
• Mol file: 122672-46-2.mol

Synonyms:2-aminocyclopentane-1-carboxylic acid;cis-2-Ac5c;cispentacin;cispentacin tosylate;cispentacin, (cis)-isomer;cispentacin, (cis-(+-))-isomer;cispentacin, (trans-(+-))-isomer;cispentacin, carboxy-(11)C-labeled;cispentacin, monopotassium salt, (cis)-isomer;cispentacin, monosodium salt, (cis)-isomer;FR 109615;FR-109615;trans-ACPC

Chemical Property of (1r,2s)-2-Aminocyclopentanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.00278mmHg at 25°C
• Boiling Point: 264.7oC at 760 mmHg
• Flash Point: 113.9oC
• PSA: 63.32000
• Density: 1.19g/cm3
• LogP: 0.89870
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 124

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S)-2-AminocyclopentanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)N)C(=O)O
• Isomeric SMILES: C1C[C@H]([C@H](C1)N)C(=O)O
• General Description: (1R,2S)-2-Aminocyclopentanecarboxylic acid, also known as (-)-Cispentacin, is a β-amino acid with a cyclopentane backbone and cis-configuration of its amino and carboxyl groups. It serves as a key structural component in certain antibiotics, such as amipurimycin, where it contributes to the N-terminal moiety. (1R,2S)-2-Aminocyclopentanecarboxylic acid can be synthesized chemoenzymatically via lipase-catalyzed kinetic resolution, enabling access to both enantiomers. Its biosynthetic role involves ATP-grasp enzyme-mediated loading, as observed in the amipurimycin pathway.

Technology Process of (1r,2s)-2-Aminocyclopentanecarboxylic acid

There total 50 articles about (1r,2s)-2-Aminocyclopentanecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1R,2S)-cis-2-benzyloxycarbonylamino-cyclopentane-1-carboxylic acid benzyl ester → (-)-cispentacin (122672-46-2,37910-65-9)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; under 760.051 Torr;

Reference yield: 95.0%

(1R,5S)-6-azabicyclo[3.2.0]heptan-7-one (39155-94-7) → (-)-cispentacin (122672-46-2,37910-65-9)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1039/P19910002276

Reference yield: 91.0%

(1R,2S)-2-phthalimidocyclopentane-1-carboxylic acid (186249-64-9) → (-)-cispentacin (122672-46-2,37910-65-9)

Guidance literature:

With methylamine; In ethanol; for 1.5h; Ambient temperature;

DOI:10.1016/S0957-4166(96)00465-X

upstream raw materials:

(1R,5S)-6-azabicyclo[3.2.0]heptan-7-one

(±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid

(-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid

(1R,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester

Downstream raw materials:

(1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid

(+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid hydrochloride

cis-(1S,2R)-2-acetylamino-cyclopentanecarboxylic acid methyl ester

C₁₂H₁₅NO₂