Introduction to Chiral or Optical Isomers: Some chemical compounds have optical activity in the sense that these compounds

have the ability to rotate the plane of polarized light. Polarized light has light waves all traveling parallel to each other. Ordinary light has light waves traveling in all directions. When polarized light is passed through a solution of an optically active compound, the plane of polarization is rotated to the right or the left. The angle of rotation can be measured in a polarimeter. An optically active organic compound can be identified by finding a chiral carbon. A chiral carbon is one that has four different "groups" attached to it. The groups can be anything from a single H to functional groups to one or more other carbons. See bromochloroiodomethane on the left - it has 3 halogens and one hydrogen. In relatively complicated compounds, each carbon must be examined carefully to determine whether it is chiral. Some compounds may have two or more chiral carbon centers such as in carbohydrates. Optical Isomers Optically active compounds exist in two isomeric forms. The isomer that rotates the plane of polarized light to the left (counterclockwise) is called levorotatory (l). The other isomer that rotates the light to the right (clockwise) is called dextrorotatory (d). The optical isomers are mirror images of each other. The isomers result from the tetrahedral geometry around the chiral carbon center. To draw mirror images, write the structure of the first isomer, draw a plane (dotted line) to represent the mirror, and finally draw the mirror image behind the plane. See the graphic on the left. Optical isomers are also designated with the letters (D) and (L) to indicate the absolute configuration. In an absolute configuration the position of the groups is compared to a commonly agreed upon standard molecule. In amino acids, this molecule is serine and for carbohydrates, it is glyceraldehyde. The capital (D) and (L) designations do not necessarily agree with the (d) or (l) designations which are based upon the actual rotation of polarized light. L-Alanine is a representative amino acid that is used in human and animal metabolism. The D isomer is not used. In the metabolism of carbohydrates only the D isomer is utilized and not the L isomer.

Carbohydrates - Isomers
Glyceraldehyde, the simplest carbohydrate, exhibits properties of a chiral or optical isomer compound. Review Chiral Compounds. This molecule forms the basis for the designation of the isomers of all of the carbohydrates.

Glyceraldehyde can exist in two isomeric forms that are mirror images of each other which are shown in the graphic on the left. The absolute configuration is defined by the molecule on the far left as the D-glyceraldehyde. With the aldehyde group in the "up" direction, the the -OH group must project to the right side of the molecule for the D isomer. Chemists have used this configuration of D-glyceraldehyde to determine the optical isomer families of the rest of the carbohydrates. All naturally occurring monosaccharides belong to the D optical family. It is remarkable that the chemistry and enzymes of all living things can tell the difference between the geometry of one optical isomer over the other.

Stereoisomerism
Studies by the German chemist Emil Fischer in the late 19th century showed that carbohydrates, such as fructose and glucose, with the same molecular formulas but with different structural arrangements and properties (i.e., isomers) can be formed by relatively simple variations of their spatial, or geometric, arrangements. This type of isomerism, which is called stereoisomerism, exists in all biological systems. Among carbohydrates, the simplest example is provided by the three-carbon aldose sugar glyceraldehyde. There is no way by which the structures of the two isomers of glyceraldehyde (see the formulas below, which are the so-called Fischer projection formulas that are commonly used to distinguish between such isomers) can be made identical, excluding breaking and reforming the linkages, or bonds, of the hydrogen (H) and hydroxyl (OH) groups attached to the carbon at position 2. The isomers are, in fact, mirror images akin to right and left hands; the term enantiomorphism is frequently employed for such isomerism. The chemical and physical properties of enantiomers are identical except for the property of optical rotation. As explained above, optical rotation is the rotation of the plane of polarized light. Polarized light is light that has been separated into two beams that vibrate at right angles to each other; solutions of substances that rotate the plane of polarization are said to be optically active, and the degree of rotation is called the optical rotation of the solution. In the case of the isomers of glyceraldehyde, the magnitudes of the optical rotation are the same, but the direction in which the light is rotatedgenerally designated as plus, or d for dextrorotatory (to the right), or as minus, or l for levorotatory (to the left)is opposite; i.e., a solution of D-(d)-glyceraldehyde causes the plane of polarized light to rotate to the right, and a solution of L-(l)-glyceraldehyde rotates the plane of polarized light to the left. Fischer projection formulas for the two isomers of glyceraldehyde are given below (see below Configuration for explanation of D and L).