127984-22-9Relevant articles and documents
Investigating chiral recognizability of diastereomeric crystallization of mandelic acid and L-phenylalanine
Kim, Jong Min,Chang, Sang Mok,Kim, In Ho,Pham, Xuan-Hung,Kim, Woo-Sik
, p. 7139 - 7147,9 (2020/08/31)
The present study investigated the mechanism of the chiral recognition of the resolving agent (L-phenylalanine) to the chiral isomers (D/L-mandelic acid). According the NMR analysis, the distinctive chemical shifts of between two diastereomer crystals (L-mandelic acid-L-phenlyalanine and D-mandelic acid-L-phenylalanine) were observed even though there was no difference of the chemicals shift of the two diastereomer solutions. This result indicated that the chiral recognition of the resolving agent mainly occurred during the crystallization of the diastereomers in the solution. Then, the chiral recognition of the diastereomers was confirmed by using thermal analysis and AFM. The diastereomer crystal of L-mandelic acid-L-phenylalanine was much more thermally stable due to the higher lattice energy than the diastereomer crystals of D-mamdelic acid-L-phenylalanine. Also, the adhesive force measured with AFM exhibited a stronger molecular interaction between L-mandelic acid and 4-amino-L-phenylalanine than between D-mandelic acid and 4-amino-L- phenylalanine. Plus, the AFM results implied that the hydroxyl group abundance on the mandelic acid surface was a possible explanation for the different chiral selectivity of the L-phenylalanine. Copyright
Stereochemical Effects in Mass Spectrometry 7. Determination of Absolute Configuration of Some Organic Molecules by Reaction Mass Spectrometry
Chen, Yao-Zu,Li, Hung,Yang, Hou-Jun,Hua, Su-Ming,Li, Hai-Quan,et al.
, p. 821 - 824 (2007/10/02)
It was found that in the chemical ionization (isobutane) mass spectra of some asymmetric secondary alcohols and α-amino acids, when a pair of enantiomers (such as R- and S-2-phenylbutyric anhydride, R- and S-mandelic acid, R- and S-2-methylbutanoic acid or R- and S-α-phenyl ethyl amine) were used as reaction reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between sample and reagent of the same configuration were much higher than those ions formed by the sample and a reagent of a different configuration. The absolute configuration of the sample molecule may be predicted by examination of mass spectra of the sample measured with R- and S-reagent respectively.This approach proved to be a convenient way for determination of the absolute configurations of organic molecules on a micromole level by mass spectrometry.