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

doi:10.3390/70400394

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

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

Stanislav Gobec^1,* and Uroš Urleb^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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(4):394-404.

Chicago/Turabian Style

Gobec, Stanislav; Urleb, Uroš. 2002. "Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423." Molecules 7, no. 4: 394-404.

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