Synthesis of L-glutamic acid labelled stereospecifically at C-3 with deuterium and non-stereospecifically at C-4 with tritium

Abstract

(2S,3S)-[3-²H₁]-, (2S,3R)-[2,3-²H₂]-, (2S,3S,4RS)-[3-²H₁,4-³H₁]-, and (2S,3R,4RS)-[2,3-²H₂,4-³H₁]-Glutamic acids have been synthesised from the corresponding labelled aspartic acids. The route involves a step where Wolff rearrangement occurs with retention of stereochemistry at a primary migrating chiral centre. The stereochemistry at C-3 of the glutamic acids has been verified by degradation to the corresponding stereospecifically labelled [²H₁] succinic acids.