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Of note, the L form of amino acids and the D form of sugars (primarily glucose) are usually the biologically reactive form. This is due to the fact that many biological molecules are chiral and thus the reactions between specific enantiomers produce pure stereoisomers. [5] Also notable is the fact that all amino acid residues exist in the L form.
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 It was withdrawn from the market when it was found to cause birth defects.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 ...
The strategy is to make these variables to interact with a chiral auxiliary (chiral selector, CS) whereby it forms a diastereomeric complex which has different physicochemical properties and makes it possible to separate the enantiomers. Based on the nature of the diastereomeric complex formed between the CS-CA species, enantiomer separation ...
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 compound's optical rotation in the (+) direction is equal to the amount of its enantiomer's rotation in the (–) direction.
For example, the two hydrogen atoms attached to the second carbon in butane are enantiotopic. Replacement of one hydrogen atom (colored blue) with a bromine atom will produce ( R )-2-bromobutane. Replacement of the other hydrogen atom (colored red) with a bromine atom will produce the enantiomer ( S )-2-bromobutane.
For example, (S-naproxen is an analgesic but the (R-isomer causes renal problems. [31] In such situations where one of the enantiomers of a racemic drug is active and the other partner has undesirable or toxic effect one may switch from racemate to a single enantiomer drug for a better therapeutic value.
Many atropisomers occur in nature, and some have applications to drug design. [20] The natural product mastigophorene A has been found to aid in nerve growth. [ 1 ] [ 21 ] Other examples of naturally occurring atropisomers include vancomycin isolated from an Actinobacterium, and knipholone , which is found in the roots of Kniphofia foliosa of ...
If R 1 and R 2 (note equation at top of page) are different substituents, there is a new stereocenter formed at the alpha position when an enol converts to its keto form. Depending on the nature of the three R groups, the resulting products in this situation would be diastereomers or enantiomers. [citation needed]