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http://hdl.handle.net/10261/20227
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Abad, José Luis | - |
dc.contributor.author | Soldevila, Carles | - |
dc.contributor.author | Camps Díez, Francisco | - |
dc.contributor.author | Clapés Saborit, Pere | - |
dc.date.accessioned | 2010-01-21T09:38:43Z | - |
dc.date.available | 2010-01-21T09:38:43Z | - |
dc.date.issued | 2003-06-05 | - |
dc.identifier.citation | Journal of Organic Chemistry 68(13): 5351-5356 (2003) | en_US |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10261/20227 | - |
dc.description | 6 pages, 2 figures, 1 scheme, 2 tables.-- PMID: 12816498 [PubMed].-- Printed version published Jun 27, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0341113 | en_US |
dc.description.abstract | A novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents is described. The key step is the kinetic lipase-catalyzed resolution of racemic mixtures of substituted propargylic alcohols. The efficiency of this new approach was tested in the preparation of the corresponding enantiomers of 1,11-hexadecandiol derivatives ((R)-5 and (S)-5). Two strategies were tested. In the first one, the racemic intermediate 1-octyn-3-ol (1) was resolved enzymatically and then elongated with 1-bromo-9,11-dioxadodecane. Alternatively, the racemic 1 can be elongated to the corresponding racemic 17,19-dioxa-7-eicosyn-6-ol (3) first and then resolved biocatalytically. Twelve commercially available lipases were screened for the kinetic resolution of these intermediates. Among them, Candida antarctica lipase (CAL-B) and Humicola lanuginosa lipase (HLL) were the best biocatalysts for the resolution of 1 (S enantiomer 90% ee, E = 35), and 3 (R enantiomer 90% ee, E = 34), respectively. | en_US |
dc.description.sponsorship | CICYT and FEDER (AGL2001-0585) and Generalitat de Catalunya (2001SGR 00342). | en_US |
dc.format.extent | 22195 bytes | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | en_US |
dc.publisher | American Chemical Society | en_US |
dc.rights | closedAccess | en_US |
dc.subject | Chemoenzymatic methodology | en_US |
dc.subject | Secondary alcohols | en_US |
dc.subject | Enzymatic resolution | en_US |
dc.subject | Sex pheromone biosynthesis | en_US |
dc.title | Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents | en_US |
dc.type | artículo | en_US |
dc.identifier.doi | 10.1021/jo0341113 | - |
dc.description.peerreviewed | Peer reviewed | en_US |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo0341113 | en_US |
dc.identifier.e-issn | 1520-6904 | - |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairetype | artículo | - |
item.cerifentitytype | Publications | - |
item.languageiso639-1 | en | - |
item.grantfulltext | none | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | No Fulltext | - |
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