1- Aminocyclopentanecarboxylic acid

Aminocyclopentanecarboxylic acid Cyclopentanone Oxalic acid dihydrate 4-Bromomethyl-2 -cyanobiphenyl Trityl chloride... 

The ethyl ester of 1-aminocyclopentanecarboxylic acid is prepared according to Adkins and Billica (J. Amer. Chem. Soc., 1948, 70, 3121). 

The ethyl ester of 1-aminocyclopentanecarboxylic acid (1.57 g) and ethyl valerimidate (1.56 g) are dissolved in 12 ml of xylene containing 6 drops of acetic acid. After refluxing for 6.5 h, the reaction medium is concentrated under vacuum, the residue is chromatographed on silica gel using a chloroform/methanol/acetic acid mixture (94/4/2 v/v/v) as the eluent. The fraction containing the expected product is evaporated several times in the presence of xylene and then benzene in order to remove the acetic acid. 1.91 g of 2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one are obtained in the form of a thick oil. 

Berlinguet, L Begin, N Babineau, L.M., Martel, F Vallee, R., Laferte, R.O. (1962). Biochemical studies of an unnatural and antitumor amino acid 1 -aminocyclopentanecarboxylic acid. Can. J. Biochem. and Physiol. 40,425-432. 

CgHiaNOa, 1-Aminocyclopentane carboxylic acid monohydrate, 38B, 171 CgHiflClNOa, 1-Aminocyclopentanecarboxylic acid hydrochloride monohydrate, 44B, 117... 

Alicyclic P-lactams 28 were successfully synthesized via a parallel liquid-phase Ugi four-center three-component reaction, starting from alicyclic P-amino acids such as cis-2-aminocyclohexanecarboxylic acid, c/.s-2-aminocyclopentanecarboxylic acid, 2,3-diexo-3-aminobicyclo-[2.2.1]heptane-2-carboxylic acid and some of their partially unsaturated analogues <02OL1967>. 

Figure 15.1 (1 R,2S)-2-Aminocyclopentanecarboxylic acid (cispentacin), (R)-pyrrolidine-3-carboxylic acid (P proline), and (7R,3S)-3-aminocyclopentanecarboxylic acid.

Essentially, nitrilases NIT-106 and NIT-107 were the most efficient catalysts, whereas NIT-lOl and NIT-105 turned out to be less suitable for the synthesis of Y-amino adds. cts-3-Aminocyclopentanecarboxylic acid (-h)-13c was prepared by Nrr-104, whereas (-)-13c was produced by NIT-106 in an enantiocomplementary manner in a high e.e. (97%) dose to the theoretical yield of a kinetic resolution. The respective trans-isomer (-)-14c was obtained in only 55% e.e. by the same enzyme. All other nitrilases examined could not enhance this result NrT-106 revealed similar outstanding sdectivities in the transformation of six-membered aminonitrile cts-( )-15a to (-)-15c in almost optical purity (>99% e.e.) and in a 29% isolated yield [43]. 

Azabicyclo[2.2.1]hept-5-en-3-one (1) has been used as a building block for the synthesis of an array of compounds with potential pharmacological applications. Either enantiomer of cw-3-aminocyclopentanecarboxylic acid (2) is accessible from a single enantiomer of (1) (eq 1). Compound (2) has been shown to act as an agonist at the y-aminobutyric acid (GABA) receptor. ... 

The absolute configuration of (+)-franj-cyclopentane-l,3-dicarboxylic acid (139) has been determined to be (IS, 3S) by the correlation with rra s-(lS, 3S)-3-aminocyclopentanecarboxylic acid (140) through the Schmidt reaction (equation 46). ... 

ABSTRACT The syntheses, transformations and some of the biological features of 2-aminocyclopentanecarboxylic acid are reviewed. The (15,2/ ) enantiomer (cispentacin) was recently isolated from different natural sources. c/s-2-Aminocyclopentacecarboxylic acid is also a component of the antibiotic amipurimycin. The paper discusses the syntheses of the racemic compounds, resolutions of the racemates and enetioselective syntheses of the title compounds. The transformations to heterocyclic compounds, applications in peptide syntheses, and biological effects are reviewed. 

Among the P-amino acid derivatives of cycloalkanes, one of the most exciting is (l/ ,25)-2-aminocyclopentanecarboxylic acid (cispentacin), an antifungal antibiotic, recently isolated independently by two Japanese groups from Bacillus cereus [2] and Streptomyces setonii [3]. 

SYNTHESES OF 2-AMINOCYCLOPENTANECARBOXYLIC ACID Syntheses of the Racemic Compound... 

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