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 |
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| Institution: | 1. Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune 411 008, India;2. NCIM, Biochemical Sciences Division, National Chemical Laboratory, Pune 411 008, India;1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Division of Materials Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan;1. Kuban State University, 149 Stavropolskaya str, Krasnodar 350040, Russian Federation;2. North Caucasus Federal University, 1a Pushkin Str, Stavropol 355009, Russian Federation |
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| Abstract: | 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. |
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