Thiocrown Ether Additive Effects on Diastereoselectivity of the Lipase-Catalyzed Reaction: Preparation of Optically Active 3-Hydroxy-2-methylalkanenitriles through a Double Enzymatic Reaction Strategy
The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselecti...
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| Published in | Bulletin of the Chemical Society of Japan Vol. 72; no. 7; pp. 1589 - 1595 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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TOKYO
The Chemical Society of Japan
01.07.1999
Chemical Soc Japan |
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| Abstract | The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy. |
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| AbstractList | The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy. Abstract The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy. |
| Author | Mitsukura, Koichi Choraku, Hiroko Da, San Thi Itoh, Toshiyuki |
| Author_xml | – sequence: 1 givenname: Koichi surname: Mitsukura fullname: Mitsukura, Koichi organization: 2 Graduate School of Natural Science and Technology, Okayama UniversityOkayama 700-8530 – sequence: 2 givenname: Hiroko surname: Choraku fullname: Choraku, Hiroko organization: 1 Department of Chemistry, Faculty of Education, Okayama UniversityOkayama 700-8530 – sequence: 3 givenname: San Thi surname: Da fullname: Da, San Thi organization: 1 Department of Chemistry, Faculty of Education, Okayama UniversityOkayama 700-8530 – sequence: 4 givenname: Toshiyuki surname: Itoh fullname: Itoh, Toshiyuki organization: 1 Department of Chemistry, Faculty of Education, Okayama UniversityOkayama 700-8530 |
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| CitedBy_id | crossref_primary_10_1002_tcr_201600016 crossref_primary_10_1021_acs_chemrev_7b00158 crossref_primary_10_1002_chem_200601043 crossref_primary_10_1002_chin_199946038 crossref_primary_10_1039_c1gc15877e crossref_primary_10_5059_yukigoseikyokaishi_69_214 |
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| Keywords | THIACROWN ETHER SECONDARY ALCOHOLS ENHANCED REACTION-RATE ASYMMETRIC-SYNTHESIS CANDIDA-RUGOSA ENANTIOSELECTIVITY PHEROMONE SYNTHESIS RESOLUTION HYDROLYSIS TRANSESTERIFICATION |
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| Snippet | The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitriles has... Abstract The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl- or... |
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| Title | Thiocrown Ether Additive Effects on Diastereoselectivity of the Lipase-Catalyzed Reaction: Preparation of Optically Active 3-Hydroxy-2-methylalkanenitriles through a Double Enzymatic Reaction Strategy |
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