Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied.
Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies / Forzato, Cristina; Benedetti, Fabio; Nitti, Patrizia; Pitacco, Giuliana; Valentin, Ennio; M., Vicario. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 12:(2001), pp. 505-511. [10.1016/S0957-4166(01)00059-3]
Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies
FORZATO, Cristina;BENEDETTI, FABIO;NITTI, PATRIZIA;PITACCO, GIULIANA;VALENTIN, ENNIO;
2001-01-01
Abstract
Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied.Pubblicazioni consigliate
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