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EnglishBoth 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.
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http://hdl.handle.net/11368/1694391| Titolo: | Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies |
| Autori interni: | FORZATO, Cristina BENEDETTI, FABIO NITTI, PATRIZIA PITACCO, GIULIANA VALENTIN, ENNIO |
| Data di pubblicazione: | 2001 |
| Rivista: | TETRAHEDRON-ASYMMETRY |
| 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. |
| Handle: | http://hdl.handle.net/11368/1694391 |
| Digital Object Identifier (DOI): | 10.1016/S0957-4166(01)00059-3 |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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