A Convergent Synthesis of Chiral Diaminopimelic Acid Derived Substrates for Mycobacterial l,d-Transpeptidases

Abstract

Amidated and deamidated chiral DAP-d-Ala analogues were prepared by olefin cross-metathesis of 12 with modified d-allylglycines using Grubbs’ 2nd generation catalyst. Hydrogenation and deprotection of these precursors provided four chiral (2S,6R)-DAP-d-alanine derivatives that were examined as substrates for Mtb l,d-transpeptidases in a ¹⁴C-d-Ala exchange reaction.

Key words

tuberculosis - Mtb l,d-transpeptidases - diaminopimelic acid - Goodman’s reagent - olefin cross-metathesis

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