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Cholic acid, a major constituent of bile, has the structure shown.

(a) Draw the structure of cholic acid, showing the rings in their chair conformations, and label each methyl group and hydroxy group as axial or equatorial. (Making a model may be helpful.)

(b) Cholic acid is secreted in bile as an amide linked to the amino group of glycine. This cholic acid-amino acid combination acts as an emulsifying agent to disperse lipids in the intestines for easier digestion. Draw the structure of the cholic acid-glycine combination and explain why it is a good emulsifying agent.

Short Answer

Expert verified

The carbon-hydrogen bonds in cyclohexane are of two types, that is, axial and equatorial. The equatorial bonds or hydrogens lie about the equator of cyclohexane ring or in the plane of the ring. The axial bonds project perpendicular to the plane of the ring. Cyclohexane is not a static structure, that is, it can undergo conformational inversion from one chair form to another. In the conformational inversion, the equatorial hydrogens become axial or vice-versa.

When the stereochemistry of the groups at the junction is same, then the chair form of both adjacent cyclohexane rings will be different so as to show proper orientation of the groups. The axial groups are labelled as 鈥渁x鈥 and equatorial groups are labelled as 鈥渆q鈥.

Step by step solution

01

Step-1. Explanation of part (a):

The carbon-hydrogen bonds in cyclohexane are of two types, that is, axial and equatorial. The equatorial bonds or hydrogens lie about the equator of cyclohexane ring or in the plane of the ring. The axial bonds project perpendicular to the plane of the ring. Cyclohexane is not a static structure, that is, it can undergo conformational inversion from one chair form to another. In the conformational inversion, the equatorial hydrogens become axial or vice-versa.

When the stereochemistry of the groups at the junction is same, then the chair form of both adjacent cyclohexane rings will be different so as to show proper orientation of the groups. The axial groups are labelled as 鈥渁x鈥 and equatorial groups are labelled as 鈥渆q鈥.

02

Step-2. Explanation of part (b):

Like a soap or detergent, this cholic acid-glycine combination has a very polar 鈥渉ead鈥 and a slightly polar 鈥渢ail鈥. The 鈥渢ail鈥 can dissolve non-polar molecules and the polar 鈥渉ead鈥 can carry the complex into polar media. That鈥檚 how it can act as a good emulsifying agent. To prevent breaking of emulsions, a small amount of emulsifying agent is added to the emulsion during its preparation. Usually, soaps, detergents, long chain sulphonic acids acts as emulsifying agents.

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