Synthesis and biological activity of 6-O-(3-acyloxytetradecanoyl)-N-acetyl-muramoyl dipeptide methyl ester and related compounds.

Synthesis and Immunoadjuvant Activity of the Phosphorylated Derivatives of 1-β-S-Acyl- and 6-O-Acyl-1-deoxy-N-acetylmuramoyl-l-alanyl-d-isoglutamine Methyl Esters

“…For example, 6-0-phosphorylation of the l-oc-O-acyl analogs of MDP, which are not active in inducing the delayed type of hypersensitivity, recovered such activity. 3) Imoto et al demonstrated that 6-O-alkylhydrogenphosphono-MDP possessed strong antitumor activity that is not found in MDP itself. 4 ) As a part of our continuing study to develop new, efficient MDP derivatives, we describe here the synthesis and biological activity of the phosphorylated derivatives of l-p-S-acyI5) and 6) which were established as being low-toxicity derivatives carrying strong immunoadjuvant activity.…”

Synthesis and Immunoadjuvant Activity of 1-α-O-, 1-β-S- and 6-O-(2-Tetradecylhexadecanoyl) Derivatives ofN-Acetylmuramoyl-l-alanyl-d-isoglutamine Methyl Ester

“…the minimum structure of mycobacteria in Freund's complete adjuvant (FCA) necessary for immunoadjuvancy.2) In the course of investigations on the structureactivity relationship of MDP, we have demonstrated that chemical modification of the functional group in the carbohydrate moiety as well as the introduction of a lipophilic character at the restricted position of the sugar skeleton produced various important effects on the manifestation of the biological activities ofMDp 3 ) l-Thio analogs of MDP,4) for example, possessed potent immunopharmacological activities but no necrosis-inducing ability, which is one of the side effects of MDP. It has also been shown that 6-0-(2-tetradecylhexadecanoyl)-MDp 5 ) caused augmentation of humoral antibody response 6 ) and, therefore, could be a good adjuvant suitable for vaccination.…”

“…Hydrolytic removal of the isopropylidene 585 group in 6 under mildly acidic condition gave 7. Treatment of8 3 ) with B30 in the presence ofDCC and DMAP yielded N- [2-…”