An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one
Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only t...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00404020_v64_n8_p1721_Monsalve |
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todo:paper_00404020_v64_n8_p1721_Monsalve2023-10-03T14:50:44Z An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one Monsalve, L.N. Machado Rada, M.Y. Ghini, A.A. Baldessari, A. 20-Pregnane succinates Candida antarctica lipase B Enzymatic stereoselective transesterification 20 pregnane succinate derivative 20beta hemisuccinyloxy 5alphah pregnan 3 one hydroxyl group pregnane derivative steroid succinic acid derivative triacylglycerol lipase unclassified drug article catalysis chemical structure enzyme isolation priority journal synthesis transesterification Candida antarctica Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only the 20β-succinyloxy derivatives are obtained. These compounds are obtained in variable yield, depending on the substitution in the ring A. The enzymatic approach allowed, for the first time, the synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one, novel compound useful as a precursor of steroid-protein conjugates. © 2007 Elsevier Ltd. All rights reserved. Fil:Monsalve, L.N. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v64_n8_p1721_Monsalve |
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Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
20-Pregnane succinates Candida antarctica lipase B Enzymatic stereoselective transesterification 20 pregnane succinate derivative 20beta hemisuccinyloxy 5alphah pregnan 3 one hydroxyl group pregnane derivative steroid succinic acid derivative triacylglycerol lipase unclassified drug article catalysis chemical structure enzyme isolation priority journal synthesis transesterification Candida antarctica |
| spellingShingle |
20-Pregnane succinates Candida antarctica lipase B Enzymatic stereoselective transesterification 20 pregnane succinate derivative 20beta hemisuccinyloxy 5alphah pregnan 3 one hydroxyl group pregnane derivative steroid succinic acid derivative triacylglycerol lipase unclassified drug article catalysis chemical structure enzyme isolation priority journal synthesis transesterification Candida antarctica Monsalve, L.N. Machado Rada, M.Y. Ghini, A.A. Baldessari, A. An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| topic_facet |
20-Pregnane succinates Candida antarctica lipase B Enzymatic stereoselective transesterification 20 pregnane succinate derivative 20beta hemisuccinyloxy 5alphah pregnan 3 one hydroxyl group pregnane derivative steroid succinic acid derivative triacylglycerol lipase unclassified drug article catalysis chemical structure enzyme isolation priority journal synthesis transesterification Candida antarctica |
| description |
Lipase-catalyzed transesterification of the 20 hydroxyl group in a series of pregnanes afforded novel 20-ethyl succinates that are not possible to prepare following the traditional synthetic methods. The reaction is stereoselective. The enzyme reacts selectively with the 20β epimers therefore only the 20β-succinyloxy derivatives are obtained. These compounds are obtained in variable yield, depending on the substitution in the ring A. The enzymatic approach allowed, for the first time, the synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one, novel compound useful as a precursor of steroid-protein conjugates. © 2007 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Monsalve, L.N. Machado Rada, M.Y. Ghini, A.A. Baldessari, A. |
| author_facet |
Monsalve, L.N. Machado Rada, M.Y. Ghini, A.A. Baldessari, A. |
| author_sort |
Monsalve, L.N. |
| title |
An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| title_short |
An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| title_full |
An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| title_fullStr |
An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| title_full_unstemmed |
An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one |
| title_sort |
efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αh-pregnan-3-one |
| url |
http://hdl.handle.net/20.500.12110/paper_00404020_v64_n8_p1721_Monsalve |
| work_keys_str_mv |
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1807315515499085824 |