Some solid state properties of enantiomers and their racemates

Chickos, James S.; Garin, David L.; Hitt, M.; Schilling, Gerhard

doi:10.1016/s0040-4020(01)97981-5

Cited by 27 publications

(22 citation statements)

References 20 publications

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“…Small differences in the IR spectra compared to those of racemic menthol, and a complex phase behavior as a function of enantiomeric composition suggest a similar structure 11. However, enantiopure and racemic menthol have very different solid‐state vapor pressures 12. This difference, just as the selective olfactory and cold‐receptor response to menthol, indicates strong chirality recognition and calls for a detailed study of the way in which menthol enantiomers and diastereoisomers differ in their interaction with other chiral molecules.…”

Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

2010

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Section: Band Positions For the Oh Stretching Vibrations Determined mentioning

confidence: 99%

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

2010

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“…The ultimate composition range is achieved if the (R=S) compound reaches twice the vapor pressure of the enantiomerically pure compound. Beyond that value, it will be thermodynamically unstable with respect to a conglomerate [29]. Somewhat opposite arguments apply if the sublimate is used instead of the residue, but in that case, one cannot improve the enantiomeric purity beyond the eutectic composition when working in the thermodynamic limit.…”

Section: Sublimation Pressure Diagramsmentioning

confidence: 99%

Chirality-dependent sublimation of -(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

Albrecht

Soloshonok

Schrader

et al. 2010

Journal of Fluorine Chemistry

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“…The (S) enantiomer accounts for the majority of the ␤-blocking effect, while the (R) enantiomer has a predominantly membrane-stabilizing effect (3,17,36,51). We hypothesized that the results for the racemate [(Ϯ)-propranolol] were different from the results for either of the enantiomers because of the difference in the physical properties between the racemate and the enantiomers (8,42).…”

Section: Vol 76 2010 Effects Of Pharmaceuticals On Aquatic Microorgmentioning

confidence: 98%

Monitoring the Effects of Chiral Pharmaceuticals on Aquatic Microorganisms by Metabolic Fingerprinting

Wharfe

Winder

Jarvis

et al. 2010

Appl Environ Microbiol

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The effects of the chiral pharmaceuticals atenolol and propranolol on Pseudomonas putida, Pseudomonas aeruginosa, Micrococcus luteus, and Blastomonas natatoria were investigated. The growth dynamics of exposed cultures were monitored using a Bioscreen instrument. In addition, Fourier-transform infrared (FT-IR) spectroscopy with appropriate chemometrics and high-performance liquid chromatography (HPLC) were employed in order to investigate the phenotypic changes and possible degradation of the drugs in exposed cultures. For the majority of the bacteria studied there was not a statistically significant difference in the organism's phenotype when it was exposed to the different enantiomers or mixtures of enantiomers. In contrast, the pseudomonads appeared to respond differently to propranolol, and the two enantiomers had different effects on the cellular phenotype. This implies that there were different metabolic responses in the organisms when they were exposed to the different enantiomers. We suggest that our findings may indicate that there are widespread effects on aquatic communities in which active pharmaceutical ingredients are present.Active pharmaceutical ingredients (APIs) and their metabolites are ubiquitous in the environment (12), and the occurrence of APIs in the aquatic environment is a growing concern (13). There are a number of routes by which APIs and their metabolites and degradation products may enter these ecosystems, and a common avenue is through excretion of the APIs and their metabolites in urine and feces. It is known that APIs have different rates of metabolism in humans. For example, the ␤-blocker propranolol is almost completely metabolized in the liver, and only 1 to 4% of an oral dose is excreted as the unchanged API and its metabolites. In contrast, 40 to 50% of an oral dose of atenolol (also a ␤-blocker) is excreted as the API or its metabolites (2, 6, 7). Subsequent degradation of the APIs and their metabolites may also occur at sewage treatment plants (STPs

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Some solid state properties of enantiomers and their racemates

Cited by 27 publications

References 20 publications

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

Chirality Recognition in Menthol and Neomenthol: Preference for Homoconfigurational Aggregation

Chirality-dependent sublimation of -(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

Monitoring the Effects of Chiral Pharmaceuticals on Aquatic Microorganisms by Metabolic Fingerprinting

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