Based on the above reaction conditions, what(and why) other natural amino acids

Question

Based on the above reaction conditions, what(and why) other natural amino acids could be used to obtain corresponding alpha-hydroxy acids without any method modifications?

Background information acids in a diazotization a-amino acids can be transformed into their corresponding a-hydroxy ao reaction and subsequent two S,2 reactions (Figure 37). L-phenyllactic acid L-phenylalanine OH NH2 SOH H2O H* SN2 (intermolecular) NaNO2/H2S04 (diazotization) SN2 (intramolecular) N2 Figure 37. Transformation of L-Phe into L-phenyllactic acid via tandem Sy2 reactions

Explanation / Answer

The given method depends solely on the diazotization of an amine group which is key to the next SN2 conversion to give an alpha-hydroxyacid with retention in configuration of the hydroxyl group as that of the amine group in the amino acid. So the presence of any other amine group or any amine-based basic functional group with free amine group will also be susceptible to this diazotization reaction except amide groups (due to their amido-imido tautomerisim decreasing the electrophilicity of the amine part of amides). Therefore, all natural amino acids except Lys and Arg can be used to generate alpha-hydroxyacids as given in the method without any changes.

Using His will also not interfere as retaining aromaticity of the imidazole will be the major retarding force for a diazotization.

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