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Topic: Functional Groups and Amino Acids  (Read 3791 times)

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Offline Sis290025

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Functional Groups and Amino Acids
« on: September 09, 2010, 07:42:26 PM »
Diagram all atoms of tryptophan as the butyl ester of N-acetyl-D-tryptophan.

I drew out N-acetyl-D-tryptophan, but I do not understand the wording of the question. What is meant by "butyl ester of N-acetyl-D-tryptophan"? Am I to imagine that N-acetyl-D-tryptophan is a participant in a chemical reaction that will yield an ester version of it?

Thank you.

Offline bromidewind

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Re: Functional Groups and Amino Acids
« Reply #1 on: September 09, 2010, 08:07:48 PM »
Maybe the butyl ester is functioning as a protecting group for the amino acid?

Offline Doc Oc

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Re: Functional Groups and Amino Acids
« Reply #2 on: September 10, 2010, 08:53:32 AM »
The question is oddly worded, that's for sure.  But it's just saying to draw N-acetyl-tryptophan with a tert-butyl ester instead of the free carboxylic acid.

Offline discodermolide

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Re: Functional Groups and Amino Acids
« Reply #3 on: September 10, 2010, 01:06:39 PM »
Diagram all atoms of tryptophan as the butyl ester of N-acetyl-D-tryptophan.

I drew out N-acetyl-D-tryptophan, but I do not understand the wording of the question. What is meant by "butyl ester of N-acetyl-D-tryptophan"? Am I to imagine that N-acetyl-D-tryptophan is a participant in a chemical reaction that will yield an ester version of it?

Thank you.

Just draw N-acetyl-D-Tryptophan and to the carboxylic acid draw a 4 carbon chain, C4H9 on the oxygen atom of the acid OH group, i.e. RCOOCH2CH2CH2CH3, where R is the rest of the molecule
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