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A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. [1] [2] This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its mirror image (not to be confused with superimposable, as any two objects ...
There are three common naming conventions for specifying one of the two enantiomers (the absolute configuration) of a given chiral molecule: the R/S system is based on the geometry of the molecule; the (+)- and (−)- system (also written using the obsolete equivalents d- and l-) is based on its optical rotation properties; and the D/L system is based on the molecule's relationship to ...
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 ...
Different enantiomers or diastereomers of a compound were formerly called optical isomers due to their different optical properties. [29] At one time, chirality was thought to be restricted to organic chemistry, but this misconception was overthrown by the resolution of a purely inorganic compound, a cobalt complex called hexol , by Alfred ...
The two enantiomers can be distinguished, for example, by the right-hand rule. This type of isomerism is called axial isomerism. Enantiomers behave identically in chemical reactions, except when reacting with chiral compounds or in the presence of chiral catalysts, such as most enzymes. For this latter reason, the two enantiomers of most chiral ...
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 ...
Enantioselective synthesis, also called asymmetric synthesis, [1] is a form of chemical synthesis.It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts."
Chiral resolution, or enantiomeric resolution, [1] is a process in stereochemistry for the separation of racemic mixture into their enantiomers. [2] It is an important tool in the production of optically active compounds, including drugs. [3] Another term with the same meaning is optical resolution.
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