Team:TU Darmstadt/Lab/ChemicalSynthesis
CHEMICAL SYNTHESIS
ABSTRACT
Since non-natural amino acids are expensive in comparison to natural amino acids we searched for a high yield synthesis method for O-methyl tyrosine. Problems with chemical alterations of amino acids to form non-natural derivates often lay in the higher reactivity of amino and carboxyl groups. For this reason both groups need to be kept in mind while searching for a possible reaction for the desired synthesis. For the protection of the amino group an acetylation reaction was used carried out to form N-acetyl tyrosine. The tested method used N-acetyl tyrosine as a reagent which was then methylated at the carboxyl group and at the hydroxyl group using dimethyl sulfate by Williamson ether synthesis. To finally form the non-natural amino acid, an acidic hydrolysis using hydrochloric acid was performed. We expected to be faced with many problems during the synthesis and also having correct interim results but since none of us is a chemical student we didn't anticipate to get a usable product from the beginning.
References
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