Cispentacin — enzymatic highlights of its 25-year history
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...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2016
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| Sorozat: | MINI-REVIEWS IN ORGANIC CHEMISTRY
13 No. 3 |
| doi: | 10.2174/1570193X13666160512141743 |
| mtmt: | 3092238 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/9919 |
| Tartalmi kivonat: | 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. © 2016 Bentham Science Publishers. |
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| Terjedelem/Fizikai jellemzők: | 219-226 |
| ISSN: | 1570-193X |