1. The two amino acids below (phenylalanine and tryptophan) are capable of react
ID: 851419 • Letter: 1
Question
1. The two amino acids below (phenylalanine and tryptophan) are capable of reacting with each other in three ways: COOH with COOH, NH2 with NH2 or COOH with NH2. What sort of synthetic 'control(s)' can we use to ensure that the COOH of the phenylalanine reacts with the NH2 of the tryptophan?
1. The two amino acids below (phenylalanine and tryptophan) are capable of reacting with each other in three ways: COOH with COOH, NH2 with NH2 or COOH with NH2. What sort of synthetic 'control(s)' can we use to ensure that the COOH of the phenylalanine reacts with the NH2 of the tryptophan?Explanation / Answer
We can react the two by protecting the undesired groups
We should protect the amino group of phenylalanine reacts by reacting it with tert-butoxycarbonyl groups which can be deprotected after reaction with the help of HBr
Similataneously we should protect the carboxylic group of tryptophan by esterification with a simple alcohol in the presence of acid and heat. The group can be deprotected after reaction of two amino groups with the help of treatment with alkali followed by acid.
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