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.

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