## Abstract The syntheses of the acyclic MDP analogs 27β37 is described, the carbohydrate moiety of muramic acid being replaced by acyclic amino alcohol structures. Their preparation was accomplished by hydrolytic cleavage of the cyclic, disubstituted 3βmorpholinones 2β5 and protection of the free
Biological activity of anomeric pairs of lipophilic glycosides ofN-acetylmuramyl-L-alanyl-D-isoglutamine
β Scribed by O. V. Kalyuzhin; A. E. Zemlyakov; N. G. Kalina; E. L. Mulik; F. N. Kuzovlev; O. V. Makarova
- Publisher
- Springer US
- Year
- 2008
- Tongue
- English
- Weight
- 324 KB
- Volume
- 145
- Category
- Article
- ISSN
- 0007-4888
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2-N-Octadecanoyl derivatives of 1-S-acetyl-, 1-S-octadecanoyl-, and of 6-O-octadecanoyl-1-S-octadecanoyl-1-thiomuramoyl-L-ala nyl-D-isoglutamine were synthesized from benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(octadecanoylamino)-beta-D-glucopy ran oside. Their immunoadjuvant activities were examined in gu
N-Acetyl-1-thiomuramoyl-L-alanyl-D-isoglutamine and some lipophilic analogs were synthesized from benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-[D-1-(methoxycarbonyl)ethyl ]- alpha-D-glucopyranoside (1). O-Debenzoylation of 2, derived from 1 by oxidation, gave 2-acetamido-2-deoxy-4,6-O-isoprop
Our synthetic study revealed that N-acetylmuramyl-L-alanyl-D-isoglutamine (l\_) is the minimum effective structure required for the immuno potentiating ability of various bacterial cell walls. However, the muramyl dipeptide (1) showed no antitumor activity based on immuno reaction, whereas cell wall