Thursday, March 24, 2011

Tryptophan

Tryptophan is an essential amino acid used by the human body. It is abreviated W or Trp and has an IUPAC name of (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid. There are two sterioisomers of tryptophan, the L and D sterioisomers, but only the L is found in the human body system, the D is only found in naturally produced peptides. Its structure is represented below.



Tryptophan has a amine group, a caboxylic acid and a indole functional group. The pKa values for each functional group are as follows:

carboxyl - 2.39
Amino - 9.39
indole - 16.2
isoelectric point - pH- 5.89

The indole ring, located on the beta carbon, is the most significant, have the capability to hyrdrogen bond donate and thus the nitrogen is often in contact with solution. Tryptophan is used as a precurser for the neurotransmiter serotonin and the vitamin niacin. The group of peptides known as cystine peptides contain tryptophan.

2 comments:

  1. You did a very good job on including all parts of the prompt. I would have liked your picture to have a white background so it would have been easier to see. I actually didn't know what an indole ring was until I read this blog. Including what reaction this part of the amino acid undergos helped with that. I would have liked to have seen you include information about the cystine peptides that contain tryptophan with a picture. Overall you did a very good job and I enjoyed reading your blog.

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