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Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423

Author(s): Stanislav Gobec | Uroš Urleb

Journal: Molecules
ISSN 1420-3049

Volume: 7;
Issue: 4;
Start page: 394;
Date: 2002;
Original page

Keywords: Muramyl dipeptide | analogues | phosphonamidates | phosphonates | immunomodulators

A syntheses of three new muramyl dipeptide (MDP) analogues related to LK 423 as potential immunomodulators are presented. The dipeptide part of the lead compound was modified by introducing a phosphonamide isostere instead of the amide bond between Lalanine and D-glutamic acid (or D-isoglutamine), yielding new MDP analogues 5 and 9. Furthermore, the amide bond between L-Ala and D-Glu was replaced by a phosphonate isostere, giving peptidyl phosphonate 14. The scope and limitations of the synthetic strategies employed are discussed.
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