A practical and scalable process for 4-(R)-hydroxycyclopent-2-en-1-(S)-acetate by desymmetrization of meso-cyclopent-2-en-1,4-diacetate catalyzed by Trichosporon beigelii (NCIM 3326), a cheap biocatalyst

Various yeast and fungal cultures from NCIM, NCL, Pune, India were screened for the hydrolysis of meso-cyclopent-2-en-1,4-diacetate 2 to 4-(R)-hydroxycyclopen-2-en-1-(S)-acetate 1 to provide a cheaper and more effective alternative to PLE which is currently being used for the conversion. Yeast cultures of Trichosporon species were identified as having a pro-R preference in the hydrolysis of 2; but the enantioselectivity was poor. Hence detailed medium-engineering investigations were made for the hydrolysis of 2 to 1 using a culture of Trichosporon beigelii (NCIM 3326) as catalyst. Addition of 10% v/v ethanol was found to enhance the enantioselectivity of the enzyme, affording 1 of 85% optical purity (op) in 83% yield. Further exploration of inherent consecutive kinetic resolutions to the desymmetrization afforded 1 of >98% op in 74% chemical yield. (C) 2000 Elsevier Science Ltd. All rights reserved.