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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
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 Muramyl dipeptide; analogues; phosphonamidates; phosphonates; immunomodulators
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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