Dynamic Kinetic Resolution of Ethyl 1,2,3,4-Tetrahydro-[beta]-carboline-1-carboxylate: Use of Different Hydrolases for Stereocomplementary Processes
Both enantiomers of 1,2,3,4-tetrahydro-[beta]-carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98% ee and 90% yield in 20 mi...
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| Veröffentlicht in: | European journal of organic chemistry 2017-09, Vol.2017 (32), p.4713 |
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| container_issue | 32 |
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| container_title | European journal of organic chemistry |
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| creator | Megyesi, Rita Mandi, Attila Kurtan, Tibor ro, Enik Fulop, Ferenc |
| description | Both enantiomers of 1,2,3,4-tetrahydro-[beta]-carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98% ee and 90% yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60% ee and 66% yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations. |
| doi_str_mv | 10.1002/ejoc.201700571 |
| format | Article |
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CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98% ee and 90% yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60% ee and 66% yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201700571</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Buffers ; Dichroism ; Enantiomers ; Hydrolysis ; Optical properties ; Optical rotation ; Selectivity</subject><ispartof>European journal of organic chemistry, 2017-09, Vol.2017 (32), p.4713</ispartof><rights>2017 WILEY-VCH Verlag GmbH & Co. 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CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98% ee and 90% yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60% ee and 66% yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700571</doi></addata></record> |
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| subjects | Buffers Dichroism Enantiomers Hydrolysis Optical properties Optical rotation Selectivity |
| title | Dynamic Kinetic Resolution of Ethyl 1,2,3,4-Tetrahydro-[beta]-carboline-1-carboxylate: Use of Different Hydrolases for Stereocomplementary Processes |
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