Abstract
Knowledge about the absolute configuration of small bioactive organic molecules is essential in pharmaceutical research because enantiomers can exhibit considerably different effects on living organisms. X-ray crystallography enables chemists to determine the absolute configuration of an enantiopure compound due to anomalous dispersion. Here, we present the determination of the absolute configuration of the flavoring agent (+)-γ-decalactone, which is liquid under ambient conditions. Single crystals were grown from the liquid in a glass capillary by in situ cryo-crystallization. Diffraction data collection was performed using Cu-Kα radiation. The absolute configuration was confirmed. The molecule consists of a linear aliphatic non-polar backbone and a polar lactone head. In the solid state, layers of polar and non-polar sections of the molecule alternating along the c-axis of the unit cell are observed. In favorable cases, this method of absolute configuration determination of pure liquid (bioactive) agents or liquid products from asymmetric catalysis is a convenient alternative to conventional methods of absolute structure determination, such as optical rotatory dispersion, vibrational circular dichroism, ultraviolet-visible spectroscopy, use of chiral shift reagents in proton NMR and Coulomb explosion imaging.
Highlights
Knowledge of the absolute configuration of small bioactive organic molecules is essential for understanding the significant different pharmacological effects of enantiomers on organisms [1,2]
Enantiomers can differ in taste and smell perception [4,5]. This applies to the natural compound discussed in this paper. γ-(+)-Decalactone [γ-lac], a compound that is liquid under ambient conditions, can be found in fruits, for example, strawberries or peaches and is suitable as a fruit flavoring agent [6,7]
Flack parameter calculated from 717 quotients of Bijvoetdispersion pairs accordTheThe absolute configuration of γ-lac was determined using anomalous efing is −0.019(60)
Summary
Knowledge of the absolute configuration of small bioactive organic molecules is essential for understanding the significant different pharmacological effects of enantiomers on organisms [1,2]. Enantiomers can differ in taste and smell perception [4,5]. This applies to the natural compound discussed in this paper. Γ-(+)-Decalactone [γ-lac], a compound that is liquid under ambient conditions, can be found in fruits, for example, strawberries or peaches and is suitable as a fruit flavoring agent [6,7]. The absolute configuration of γ-lac has a significant influence on olfactory and taste perception.
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