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Abstract:

The preparation of a series of novel chiral N-(2-hydroxylalkyl)-acrylamides through a lipase-catalyzed resolution of racemic alkanolamines is described. The absolute stereochemistry and enantiomeric excess of the products were determined by a modified Mosher's method. The method was validated for this particular case by the synthesis of an enantiomerically pure product. Moreover, the stereoselective behavior of the lipase in this reaction is discussed. © 2011 Informa UK, Ltd.

Registro:

Documento: Artículo
Título:Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides
Autor:Monsalve, L.N.; Rustoy, E.M.; Baldessari, A.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Ciudad Universitaria, Pabellán 2, Piso 3, C1428EGA, Buenos Aires, Argentina
Palabras clave:Candida antarctica lipase B; Mosher' s method; N-(hydroxyalkyl)-acrylamides; primary alcohol; stereoselectivity; Enantiomers; Absolute stereochemistry; Acrylamides; Biocatalytic synthesis; Candida antarctica lipase B; Enantiomeric excess; Lipase-catalyzed resolution; Mosher' s method; Primary alcohols; Stereoselectivity; acrylamide derivative; alkanolamine; triacylglycerol lipase; aminolysis; article; biocatalysis; Candida antarctica; catalyst; chemical reaction; chirality; enantiomer; enantioselectivity; enzyme mechanism; enzyme specificity; Mosher method; nonhuman; reliability; stereochemistry; structure analysis; synthesis; technique; Candida antarctica
Año:2011
Volumen:29
Número:2-3
Página de inicio:87
Página de fin:95
DOI: http://dx.doi.org/10.3109/10242422.2011.578212
Título revista:Biocatalysis and Biotransformation
Título revista abreviado:Biocatal. Biotransform.
ISSN:10242422
CODEN:BOBOE
CAS:triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v29_n2-3_p87_Monsalve

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Citas:

---------- APA ----------
Monsalve, L.N., Rustoy, E.M. & Baldessari, A. (2011) . Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides. Biocatalysis and Biotransformation, 29(2-3), 87-95.
http://dx.doi.org/10.3109/10242422.2011.578212
---------- CHICAGO ----------
Monsalve, L.N., Rustoy, E.M., Baldessari, A. "Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides" . Biocatalysis and Biotransformation 29, no. 2-3 (2011) : 87-95.
http://dx.doi.org/10.3109/10242422.2011.578212
---------- MLA ----------
Monsalve, L.N., Rustoy, E.M., Baldessari, A. "Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides" . Biocatalysis and Biotransformation, vol. 29, no. 2-3, 2011, pp. 87-95.
http://dx.doi.org/10.3109/10242422.2011.578212
---------- VANCOUVER ----------
Monsalve, L.N., Rustoy, E.M., Baldessari, A. Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides. Biocatal. Biotransform. 2011;29(2-3):87-95.
http://dx.doi.org/10.3109/10242422.2011.578212