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

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 L-alanine and D-glutamic acid (or D-isoglutamine),...

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Autores principales: Gobec, Stanislav, Urleb, Uroš
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2002
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146478/
http://dx.doi.org/10.3390/70400394
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author Gobec, Stanislav
Urleb, Uroš
author_facet Gobec, Stanislav
Urleb, Uroš
author_sort Gobec, Stanislav
collection PubMed
description 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 L-alanine 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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spelling pubmed-61464782018-11-19 Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423 Gobec, Stanislav Urleb, Uroš Molecules Article 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 L-alanine 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. MDPI 2002-05-02 /pmc/articles/PMC6146478/ http://dx.doi.org/10.3390/70400394 Text en © 2002 by MDPI (http://www.mdpi.org). Reproduction is permitted for non commercial purposes.
spellingShingle Article
Gobec, Stanislav
Urleb, Uroš
Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title_full Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title_fullStr Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title_full_unstemmed Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title_short Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
title_sort synthesis of new lipophilic phosphonate and phosphonamidate analogues of n-acetylmuramyl-l-alanyl-d-isoglutamine related to lk 423
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146478/
http://dx.doi.org/10.3390/70400394
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AT urleburos synthesisofnewlipophilicphosphonateandphosphonamidateanaloguesofnacetylmuramyllalanyldisoglutaminerelatedtolk423

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