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Cispentacin - Enzymatic Highlights of its 25-Year History

[ Vol. 13 , Issue. 3 ]

Author(s):

Eniko Forro and Ferenc Fulop   Pages 219 - 226 ( 8 )

Abstract:


Because of its natural occurrence and novel biological activity, interest in the investigation of (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin) has rapidly increased. Since its activity against Candida albicans, C. neoformans, and a systemic C. infection, a number of enzymatic strategies for its preparation in enantiomerically pure form have been developed. Structural optimization of cispentacin resulted in the synthesis of derivatives such as (1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid with even superior efficacy in view of antifungal activity. Not only cispentacin itself and some of its small-molecule derivatives have been described as molecules of interesting bioactivity but it was also found that the cyclopentane β-amino acid moiety may be a key element of larger molecules with important pharmacological properties, such as the antibiotic amipurimycin. The present review is intended to give a brief insight into the most relevant enzymatic strategies for the synthesis of 25-year-old cispentacin and its close analogues containing the cispentacin subunit. These methods are classified as indirect or direct strategies. Some practical details for the preparative-scale resolution of a selected racemate furnishing cispentacin with excellent ee and very good yield are highlighted at the end of this overview.

Keywords:

β-Amino ester, β-lactam, chemro-enzymatic synthesis, cispentacin, cyclic β-amino acid, enzymatic catalysis.

Affiliation:

Institute of Pharmaceutical Chemistry and Stereochemistry Research Group of the Hungarian, Academy of Sciences University of Szeged, H-6720 Szeged, Eotvos u. 6, Hungary.

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