PNNL

Abstract

We report an unexpected synthesis of methyl-2-(diphenylmethyleneamino)acrylate (12) enroute the process of brominating the hydroxy group of serine. 12, an excellent Michael acceptor, has been reported in the use of substituted tryptophan synthesis via Friedel Craft’s alkylation using AlCl3. We have applied it to the synthesis of an alkyne-substituted unnatural tryptophan analog. The alkynylated tryptophan performs as a chemical probe by its incorporation into actively translating Escherichia coli cells, whereby the alkyne moiety enables multimodal analyses through click chemistry mediated attachment of reporting groups.