Control analysis of complex real-world samples of vegetables origin requires to develop ever more rapid and accurate enantiomer recognition routine methods. Recently short and narrow bore columns have been proposed as an approach to overcome the long analysis time required by enantioselective (ES)-GC with cyclodextrins derivatives (CD) as chiral selectors for routine analyses. New CDs with better enantioselectivity and/or specific for compounds with similar structural characteristics and/or functionality at the same time giving resolutions for the investigated enantiomers above 1.5 to enable a correct enantiomeric excess and ratio determination, have therefore to be developed to speed-up Es-GC analysis . Asymmetric persubstituted methyl/ethyl CD ( 6I-VII-O-TBDMS- 3I-VII-O-ethyl-2I-VII-O-methyl / 3I-VII-O-methyl-2I-VII-O-ethyl-β-cyclodextrin) were recently described showing better enantiomer resolution and increased number of separated chiral compounds, proving to be useful in routine analysis of matrices with several chiral markers in a single run. This poster describes synthesis and evaluation of the enantioselective performances of a new asymmetric CD, 6I-VII-O-TBDMS-3I-VIIO-acetyl-2I-VII-O-methyl-β-CD, for the separation of medium-to-high volatility racemates in the flavour and fragrance field and in the chiral recognition of markers of real-world samples. Its performances are compared to those of cited new asymmetrical derivatives not only in terms of total enantioselectivity but also of increase of resolution of classes or groups of compounds diagnostic for specific applications. The methyl/acetyl CD derivative shows very good enantioselectivity for compounds with carbonyl groups, increasing both the number of separated compounds and resolutions. This characteristic afforded to reduce column length and increase temperature rates resulting in a significant speeding-up of the analyses of matrices, such as fruit flavours, characterized by carbonyl compounds (lactones, ketones and aldehydes).
New asymmetrical persubstituted cyclodextrins: 2-O-methyl-3-O-acetyl-6-O-t-butyl dimethylsilyl-β-derivative as chiral selector for Enantioselective Gas Chromatography of carbonylic chiral compounds in the flavour and fragrance field
LIBERTO, Erica;CAGLIERO, Cecilia Lucia;CORDERO, Chiara Emilia Irma;SGORBINI, Barbara;RUBIOLO, Patrizia;CRAVOTTO, Giancarlo;BICCHI, Carlo
2010-01-01
Abstract
Control analysis of complex real-world samples of vegetables origin requires to develop ever more rapid and accurate enantiomer recognition routine methods. Recently short and narrow bore columns have been proposed as an approach to overcome the long analysis time required by enantioselective (ES)-GC with cyclodextrins derivatives (CD) as chiral selectors for routine analyses. New CDs with better enantioselectivity and/or specific for compounds with similar structural characteristics and/or functionality at the same time giving resolutions for the investigated enantiomers above 1.5 to enable a correct enantiomeric excess and ratio determination, have therefore to be developed to speed-up Es-GC analysis . Asymmetric persubstituted methyl/ethyl CD ( 6I-VII-O-TBDMS- 3I-VII-O-ethyl-2I-VII-O-methyl / 3I-VII-O-methyl-2I-VII-O-ethyl-β-cyclodextrin) were recently described showing better enantiomer resolution and increased number of separated chiral compounds, proving to be useful in routine analysis of matrices with several chiral markers in a single run. This poster describes synthesis and evaluation of the enantioselective performances of a new asymmetric CD, 6I-VII-O-TBDMS-3I-VIIO-acetyl-2I-VII-O-methyl-β-CD, for the separation of medium-to-high volatility racemates in the flavour and fragrance field and in the chiral recognition of markers of real-world samples. Its performances are compared to those of cited new asymmetrical derivatives not only in terms of total enantioselectivity but also of increase of resolution of classes or groups of compounds diagnostic for specific applications. The methyl/acetyl CD derivative shows very good enantioselectivity for compounds with carbonyl groups, increasing both the number of separated compounds and resolutions. This characteristic afforded to reduce column length and increase temperature rates resulting in a significant speeding-up of the analyses of matrices, such as fruit flavours, characterized by carbonyl compounds (lactones, ketones and aldehydes).
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