Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic b,b-dialkyl-c-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active c-nitroesters gave access to optically active b,b-disubstituted c-aminoacids as well as a,a-disubstituted succinic acids, both being biologically relevant compounds.
Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom / F., Felluga; Ghelfi, Franco; G., Pitacco; Roncaglia, Fabrizio; E., Valentin; C. D., Venneri. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 21:17(2010), pp. 2183-2191. [10.1016/j.tetasy.2010.07.010]
Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom.
GHELFI, Franco;RONCAGLIA, Fabrizio;
2010
Abstract
Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic b,b-dialkyl-c-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active c-nitroesters gave access to optically active b,b-disubstituted c-aminoacids as well as a,a-disubstituted succinic acids, both being biologically relevant compounds.
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