(1S,3R)-3-aminocyclopentanecarboxylic acid, CAS No. 71830-07-4

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71830-07-4

Catalog No. EBD893899

CAS 71830-07-4

Name (1S,3R)-3-aminocyclopentanecarboxylic acid

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Basic Information

Synonyms: (1S,3R)-3-aminocyclopentanecarboxylicacid (+)-(1R,3S)-1-amino-cyclopent-2-ene-4-carboxylicacid L-AcPAC (+)-(1S,3R)-3-Aminocyclopentanecarboxylicacid (+)-(1s,3r)-b-homocycloleucine (+)-(1s,3r)-beta-homocycloleucine (1r,3r)-3-amino-cyclopentanecarboxylicacid (1s,3r)-3-amino-cyclopentanecarboxylicacid (1s,3r)-3-aminocyclopentanecarboxylicacid,(e.e.) cyclopentanecarboxylicacid,3-amino-,(1s,3r)-(9ci)

Molecular Formula: C6H11NO2

Molecular Weight: 129.16

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(1S,3R)-3-Aminocyclopentanecarboxylic acid is a chiral, non-proteinogenic amino acid featuring both an amino group and a carboxylic acid group on a cyclopentane ring. Its specific stereochemistry (1S,3R) makes it a valuable constrained scaffold in medicinal chemistry. This compound serves as a key chiral building block in the synthesis of pharmaceutical agents. Its primary application is as a crucial intermediate for the production of potent antiviral drugs, most notably for the synthesis of carbocyclic nucleoside analogues. These analogues are investigated for their activity against viruses such as hepatitis B virus (HBV) and human immunodeficiency virus (HIV). The rigid cyclopentane backbone mimics the sugar moiety of natural nucleosides, contributing to metabolic stability and target binding. As a bifunctional molecule containing amine and carboxylic acid groups, it is readily amenable to further chemical modifications, enabling its incorporation into more complex molecular architectures. It is typically handled as a white to off-white solid and requires storage under inert conditions to maintain stability.

Physical Properties

Melting Point: 192 °C

Boiling Point: 264.7ºC at 760 mmHg

Flash Point: 113.9 ºC

Density: 1.19 g/cm3

Analytical Data

Appearance: white to off-white crystalline powder