Hydroxy- and aminomethylation reactions in the formation of oligomers from l-tyrosine and formaldehyde in basic medium
2014
Nuñez-Dallos, Nelson | Díaz-Oviedo, Christian | Quevedo, Rodolfo
The study of the reaction of l-tyrosine or its tetrabutylammonium salt with formaldehyde was performed. The results established that this reaction does not lead to macrocyclic amino acid-type compounds, and in all cases, mixtures of linear oligomers of two or more l-tyrosine units bound by methylene groups were obtained. The formation of ion pair-type linear aggregates in the tetrabutylammonium salt hinders the oligomerization reaction, allowing the isolation of an l-tyrosine dimer, unlike the l-tyrosine reaction, in which a trimer could be isolated.In this Letter, the behavior of different l-tyrosine derivatives with formaldehyde is analyzed, and the conditions that direct the reaction course toward macrocyclic or linear compounds are discussed.
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