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That is, on reflecting the meso compound through a mirror plane perpendicular to the screen, the same stereochemistry is obtained; this is not the case for the non-meso tartaric acid, [3] which generates the other enantiomer. The meso compound must not be confused with a 50:50 racemic mixture of the two optically-active compounds, although ...
An example of such an enantiomer is the sedative thalidomide, which was sold in a number of countries around the world from 1957 until 1961. It was withdrawn from the market when it was found to cause birth defects. One enantiomer caused the desirable sedative effects, while the other, unavoidably [23] present in equal quantities, caused birth ...
Another excellent, though not high-yielding, example is the kinetic resolution of (±)-8-amino-5,6,7,8-tetrahydroquinoline. When exposed to Candida antarctica lipase B (CALB) in toluene and ethyl acetate for 3–24 hours, normal kinetic resolution occurs, resulting in 45% yield of 97% ee of starting material and 45% yield of >97% ee acylated ...
Pure enantiomers also exhibit the phenomenon of optical activity and can be separated only with the use of a chiral agent. In nature, only one enantiomer of most chiral biological compounds, such as amino acids (except glycine, which is achiral), is present. Enantiomers differ by the direction they rotate polarized light: the amount of a chiral ...
This creates a 1:1 molar ratio of enantiomers and is referred to as a racemic mixture (i.e. contain equal amount of (+) and (−) forms). Plus and minus forms are called Dextrorotation and levorotation. [1] The D and L enantiomers are present in equal quantities, the resulting sample is described as a racemic mixture or a racemate. Racemization ...
For example, of the naturally occurring amino acids, all are L, and most are (S). For some molecules the (R)-enantiomer is the dextrorotary (+) enantiomer, and in other cases it is the levorotary (−) enantiomer. The relationship must be determined on a case-by-case basis with experimental measurements or detailed computer modeling. [7]
An enantiomeric pair (S,S)- and (R,R)-ethambutol, along with the achiral stereoisomer called meso-form, it holds a diastereomeric relationship with the optically active stereoisomers. The activity of the drug resides in the (S,S)-enantiomer which is 500 and 12 fold more potent than the (R,R)-ethambutol and the meso-form. The drug had initially ...
For example, the specific rotation of (S)-2-ethyl-2-methyl succinic acid is found to be dependent on concentration; in what is known as the Horeau effect [3] the relationship between mole based ee and optical rotation based ee can be non-linear i.d. in the succinic acid example the optical activity at 50% ee is lower than expected.