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Synthesis 2012; 44(19): 3043-3048
DOI: 10.1055/s-0032-1316774
DOI: 10.1055/s-0032-1316774
paper
A Convergent Synthesis of Chiral Diaminopimelic Acid Derived Substrates for Mycobacterial l,d-Transpeptidases
Further Information
Publication History
Received: 30 April 2012
Accepted after revision: 11 June 2012
Publication Date:
29 August 2012 (online)
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-metathesisSupporting Information
- Supplementary material including additional experimental details and 1H NMR spectra for all compounds is available online at http://www.thieme-connect.com/ ejournals/toc/synthesis.
- Supporting Information
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