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N-Acetylmuramyl-L-Alanyl-D-Isoglutamine Glycosides: Effect of Glycoside Bond Configuration and Aglycone on Biological Activity

Abstract

Hexyl, octyl, and cyclohexyl β-glycosides and heptyl and cyclohexyl α-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP α-glycosides in comparison with the corresponding β-glycosides and MDP itself. In the case of alkyl β-glycosides, differences in hydrocarbon chain lengths (C4–C8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

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Correspondence to V. Ya. Chirva.

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Zemlyakov, A.E., Tsikalov, V.V., Kalyuzhin, O.V. et al. N-Acetylmuramyl-L-Alanyl-D-Isoglutamine Glycosides: Effect of Glycoside Bond Configuration and Aglycone on Biological Activity. Russian Journal of Bioorganic Chemistry 29, 286–292 (2003). https://doi.org/10.1023/A:1023944818406

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  • DOI: https://doi.org/10.1023/A:1023944818406

  • glycopeptides
  • muramyl dipeptide
  • muramyl dipeptide glycosides
  • immunostimulating activity
  • nonspecific infectious resistance