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However, compounds that contain an even number of asymmetric atoms sometimes lack chirality because they are arranged in mirror-symmetric pairs, and are known as meso compounds. For instance, meso tartaric acid (shown on the right) has two asymmetric carbon atoms, but it does not exhibit enantiomerism because there is a mirror symmetry plane.
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 ...
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 ...
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 ...
A meso compound is superposable on its mirror image, therefore it reduces the number of stereoisomers predicted by the 2 n rule. This occurs because the molecule obtains a plane of symmetry that causes the molecule to rotate around the central carbon–carbon bond. [12] One example is meso-tartaric acid, in which (R,S) is the same as the (S,R) form
1,2,3,4-Butanetetracarboxylic acid is an organic compound with the formula HO 2 CCH 2 CH(CO 2 H)CH(CO 2 H)CH 2 CO 2 H. It is one of the simplest stable tetracarboxylic acids. The compound exists as two diastereomers, meso and the (R,R)/(S,S) pair. All are white solids. The compound is produced by oxidation of tetrahydrophthalic anhydride. [1]
An opposite trend is observed in desymmetrizing hydrolyses of 2-methyl malonates, which afford the (S) enantiomer when the other substituent on C-2 is small, and the (R) enantiomer when the other C-2 substituent is large. [7] (5) A number of meso diesters other than the substrates described above may be hydrolyzed by PLE with high ...
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.