Thursday, March 24, 2011

Amino Acid

Glutamic acid is one of the twenty proteinogenic amino acids. It can be abbreviated either Glu or E. This amino acid is a non-essential amino acid. Glutamic acid is a key molecule in cellular metabolism, and is abundant in both animal and plant protein. However, in humans it is a non-essential amino acid because the body is able to produce it's own glutamic acid. In addition to this, the dietary proteins are broken down by digestion into amino acids which play as a metabolic fuel for other functional roles in the body.  A picture of glutamic acid is shown below:

The pKa value of carboxyl group for glutamic acid in a polypeptide is about 4.3. This may be a little high for a pKa value due to the inductive effect of the additional methylene group. The isoelectric point is around 5.65. Pka values are shown below in the diagram:
Chemical structure for glutamic acid 

Glutamic acid can be easily converted to proline; due to the carboxyl group is reduced to the aldehyde. From here the aldehyde can react with the alpha-amino group which eliminates water. A diagram of this is shown below:
Glutamic acid to Glutamate Semialdehyde to pyrroline 5-carboxylate to Proline

2 comments:

  1. I felt like your blog was missing a few things. You did not include a specific polypeptide that contains glutamic acid. I believe this was a very important part of the assignment. The closest that I saw you came was mentioning the pKa of glutamic acid in a polypeptide. Also, you did not mention the isoelectric point. I know that I could calculate it myself, but it is more of a convenience thing. I did, however, think you did a solid job on including illustrations so your readers can see your amino acid. This helps in their understand of the material.

    -The High School Chemist

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  2. I liked the conversion of glutamate to proline, but a bit more detail of what catalyzes this reaction would have been helpful.

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