Difference between alpha-keto acid and keto acid

In summary, alpha-keto acid contains an alpha carbon while keto acid does not have an alpha carbon. Alpha carbon is found in other cases as well. Alpha and beta carbons are used in chemistry to refer to sugars with different naming conventions.
  • #1
soopo
225
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Homework Statement


What is the difference between alpha-keto acid and keto acid?

The Attempt at a Solution


I know that the difference is that alpha-keto acid contains an alpha carbon.
However, I do not know what the alpha carbon is in this case, and how I can show it.
 
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  • #2
What is alpha carbon in other cases?
 
  • #3
Borek said:
What is alpha carbon in other cases?

You can have alpha carbon, for example, in glucose and maltose.
 
  • #4
What makes this carbon 'alpha'? Why is it called this way? How does it differ from 'beta'?
 
  • #5
Borek said:
What makes this carbon 'alpha'? Why is it called this way? How does it differ from 'beta'?

I found the answer in Wikipedia.
Alpha keto-acid has keto group next to COOH, while beta keto-acid has keto group at the second Carbon from COOH.

The LHS molecule is alpha-keto acid, while RHS is beta-keto acid in the following picture.
http://dl.getdropbox.com/u/175564/alpha-beta-acids.png

Note that keto group in the RHS molecule is at the third carbon that is the second C from COOH.

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Is everything correct?
 
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  • #6
If you were looking for the answer in wikipedia, it would be better to start at the very beginning:

http://en.wikipedia.org/wiki/Alpha_carbon

soopo said:
The LHS molecule is alpha-keto acid, while RHS is beta-keto acid in the following picture.
http://dl.getdropbox.com/u/175564/alpha-beta-acids.png

Other left.
 
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  • #7
Borek said:
If you were looking for the answer in wikipedia, it would be better to start at the very beginning:

http://en.wikipedia.org/wiki/Alpha_carbon

Thank you!

So we have both alpha and beta carbons in both molecules
http://dl.getdropbox.com/u/175564/alpha-beta-carbons-updated.png

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Is the carbons now correctly labeled with alpha and beta carbons?
 
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  • #8
OK now.

As you see concept of 'alpha'. 'beta' and 'gamma' carbons is widely used in chemistry. Not very formal, often very useful.
 
  • #9
Borek said:
OK now.

As you see concept of 'alpha'. 'beta' and 'gamma' carbons is widely used in chemistry. Not very formal, often very useful.

I am unsure about alpha and beta carbons in http://www.laakis.com/wp-content/uploads/2008/12/picture-7.png" .

It seems that the same naming convention does not apply here.
Instead, the position of OH group seems to determine the name.
 
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  • #10
soopo said:
It seems that the same naming convention does not apply here.

Yes. As I told you - it is not formal. Still, widely used. See GHB for example.
 
  • #11
The alpha and beta conventions for sugars is completely different from the alpha, beta, gamma, etc. nomenclature that you were discussing previously.

For cyclic sugars, alpha refers to a cyclized sugar in which the OH group of the anomeric carbon (the carbon with two bonds to oxygen) is on the opposite side of the ring as the alkyl group on the ring.
 
  • #12
Ygggdrasil said:
The alpha and beta conventions for sugars is completely different from the alpha, beta, gamma, etc. nomenclature that you were discussing previously.

For cyclic sugars, alpha refers to a cyclized sugar in which the OH group of the anomeric carbon (the carbon with two bonds to oxygen) is on the opposite side of the ring as the alkyl group on the ring.

Thank you both!
 

What is the difference between alpha-keto acid and keto acid?

Alpha-keto acid and keto acid are both types of organic compounds that contain a carbonyl group (-C=O). However, the difference lies in the position of this group on the carbon chain. In alpha-keto acids, the carbonyl group is attached to the carbon atom next to the carboxyl group (-COOH), while in keto acids, the carbonyl group is attached to any other carbon atom on the chain.

What are some examples of alpha-keto acids and keto acids?

Some examples of alpha-keto acids include pyruvic acid, which is a key intermediate in cellular respiration, and alpha-ketoglutaric acid, which is involved in the citric acid cycle. Examples of keto acids include acetoacetic acid, which is produced during ketosis, and phenylpyruvic acid, which is a byproduct of phenylalanine metabolism.

How do alpha-keto acids and keto acids differ in terms of chemical properties?

Due to the position of the carbonyl group, alpha-keto acids tend to be more reactive than keto acids. This is because the proximity of the carbonyl group to the carboxyl group allows for easier formation of enol forms, which are more reactive than keto forms. Additionally, alpha-keto acids are more acidic than keto acids due to the presence of the carboxyl group.

What are the biological functions of alpha-keto acids and keto acids?

Both alpha-keto acids and keto acids play important roles in various biological processes. For example, alpha-ketoglutaric acid is involved in amino acid metabolism, while acetoacetic acid is a source of energy during periods of fasting or low carbohydrate intake. Additionally, some keto acids, such as oxaloacetic acid, act as intermediates in metabolic pathways.

Can alpha-keto acids and keto acids be converted into one another?

Yes, alpha-keto acids can be converted into keto acids through a process called keto-enol tautomerism. In this process, the carbonyl group in the alpha-keto acid shifts to a different position on the carbon chain, creating a keto acid. However, this conversion is reversible and can occur multiple times, depending on the conditions of the reaction.

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