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Molecules 2002, 7(4), 394-404; doi:10.3390/70400394
Article

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

1,*  and 1,2
1 University of Ljubljana, Faculty of Pharmacy, Aškerčeva 7, 1000 Ljubljana, Slovenia 2 Lek d.d., Verovškova 57, 1000 Ljubljana, Slovenia
* Author to whom correspondence should be addressed.
Received: 9 January 2002 / Revised: 2 May 2002 / Accepted: 2 May 2002 / Published: 2 May 2002
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Abstract

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.
Keywords: Muramyl dipeptide; analogues; phosphonamidates; phosphonates; immunomodulators Muramyl dipeptide; analogues; phosphonamidates; phosphonates; immunomodulators
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Gobec, S.; Urleb, U. Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423. Molecules 2002, 7, 394-404.

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