Chapter 26: Problem 15

Bile acids, used to aid digestion of fats, differ from most other steroids in that they have a cis configuration at the junction of rings \(A\) and \(B\).

Short Answer

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Answer: Bile acids have a cis configuration at the junction of rings A and B, which is unique compared to most other steroids that have a trans configuration. This cis configuration allows bile acids to be more effective at binding and emulsifying fats, playing a crucial role in their function in aiding the digestion and absorption of fats.

Step by step solution

Understand cis and trans isomers

Cis and trans isomers are two isomers where the same functional groups or atoms are present in a molecule but have a different arrangement or orientation around a double bond or a rigid ring system. This difference in arrangement can lead to different physical and chemical properties. In the context of bile acids, a cis configuration means that the groups or atoms attached to the junction between rings A and B are on the same side. In contrast, a trans configuration means the groups or atoms are on the opposite sides of the junction.

Identify rings A and B in bile acids

Bile acids are derivatives of steroids, meaning they have a four-ring structure made of three six-membered rings (A, B, and C) and one five-membered ring (D). In this exercise, we are concerned with the junction between rings A and B, which are the first two six-membered rings of the steroid structure.

Understand the role of bile acids in digestion and their structure

Bile acids are produced in the liver and play a critical role in the digestion and absorption of fats and fat-soluble vitamins. They act as biological detergents by breaking down large fat globules into small, more manageable micelles, increasing the surface area for lipase enzymes to act upon. The primary bile acids are cholic acid and chenodeoxycholic acid, both of which have a cis configuration at the junction of rings A and B. This cis configuration is essential for the acids' ability to bind fats and solubilize them in the aqueous environment of the intestines.

Compare bile acids with other steroids

Most steroids have a trans configuration at the junction of rings A and B, which can result in different biological functions and properties. An example of this is cholesterol, which has a trans configuration and is a precursor for other steroids, including bile acids. The cis configuration in bile acids allows them to be more effective at binding and emulsifying fats. In conclusion, bile acids have a cis configuration at the junction of rings A and B, making it different from most other steroids. This unique configuration plays a vital role in their function to aid in the digestion and absorption of fats.

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Bile acids, used to aid digestion of fats, differ from most other steroids in that they have a cis configuration at the junction of rings \(A\) and \(B\).

Short Answer

Step by step solution

Understand cis and trans isomers

Identify rings A and B in bile acids

Understand the role of bile acids in digestion and their structure

Compare bile acids with other steroids

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