N-acetylmuramyl-L-alanyl-D-isoglutamine glycosides. Effect of glycoside center configuration and aglycone nature on biological activity

Zemliakov, A.E.; Tsikalov, V.V.; Kaliuzhin, O.V.; Kur'ianov, V.O.; Chirva, V.I.; Zemliakov, A.E; Tsikalov, V.V; Kaliuzhin, O.V; Kur&apo; ianov, V.O; Chirva, V.I

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N-acetylmuramyl-L-alanyl-D-isoglutamine glycosides. Effect of glycoside center configuration and aglycone nature on biological activity

Zemliakov, A.E.; Tsikalov, V.V.; Kaliuzhin, O.V.; Kur'ianov, V.O.; Chirva, V.I.

Bioorganicheskaia Khimiia 29(3): 316-322

2003

ISSN/ISBN: 0132-3423

PMID: 12845808

Document Number: 564446

Hexyl, octyl, and cyclohexyl beta-glycosides and heptyl and cyclohexyl alpha-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP alpha-glycosides in comparison with the corresponding beta-glycosides and MDP itself. In the case of alkyl beta-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.