What are Isomers?

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What are Isomers? (Campbell Biology)

Variation in the architecture of organic molecules can be seen in isomers, compounds that have the same numbers of atoms of the same elements but different structures and hence different properties. We will examine three types of isomers: structural isomers, cis-trans isomers, and enantiomers.

Structural isomers differ in the covalent arrangements of their atoms. Compare, for example, the two five-carbon compounds in. Both have the molecular formula C5H12, but they differ in the covalent arrangement of their carbon skeletons. The skeleton is straight in one compound but branched in the other. The number of possible isomers increases tremendously as carbon skeletons increase in size. There are only three forms of C5H12, but there are 18 variants of C8H18 and 366,319 possible structural isomers of C20H42. Structural isomers may also differ in the location of double bonds.

In cis-trans isomers, carbons have covalent bonds to the same atoms, but these atoms differ in their spatial arrangements due to the inflexibility of double bonds. Single bonds allow the atoms they join to rotate freely about the bond axis without changing the compound. In contrast, double bonds do not permit such rotation. If a double bond joins two carbon atoms, and each C also has two different atoms (or groups of atoms) attached to it, then two distinct cis-trans isomers are possible. Consider a simple molecule with two double-bonded carbons, each of which has an H and an X attached to it. The arrangement with both Xs on the same side of the double bond is called a cis isomer, and that with the Xs on opposite sides is called a trans isomer. The subtle difference in shape between such isomers can have a dramatic effect on the biological activities of organic molecules. For example, the biochemistry of vision involves a light-induced change of retinal, a chemical compound in the eye, from the cis isomer to the trans isomer.

Enantiomers are isomers that are mirror images of each other and that differ in shape due to the presence of an asymmetric carbon, one that is attached to four different atoms or groups of atoms. The four groups can be arranged in space around the asymmetric carbon in two different ways that are mirror images. Enantiomers are, in a way, left-handed and right-handed versions of the molecule. Just as your right hand won’t fit into a left-handed glove, a “right-handed” molecule won’t fit into the same space as the “left-handed” version. Usually, only one isomer is biologically active because only that form can bind to specific molecules in an organism.

The concept of enantiomers is important in the pharmaceutical industry because the two enantiomers of a drug may not be equally effective, as is the case for both ibuprofen and the asthma medication albuterol. Methamphetamine also occurs in two enantiomers that have very different effects. One enantiomer is the highly addictive stimulant drug known as “crank,” sold illegally in the street drug trade. The other has a much weaker effect and is the active ingredient in an over-the-counter vapor inhaler for treatment of nasal congestion. The differing effects of enantiomers in the body demonstrate that organisms are sensitive to even the subtlest variations in molecular architecture. Once again, we see that molecules have emergent properties that depend on the specific arrangement of their atoms.

Source:

Urry, Lisa A.. Campbell Biology. Pearson Education. Kindle Edition. https://www.pearson.com/us/higher-education/series/Campbell-Biology-Series/2244849.html

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