Synthesis of immunologically Active Muramyl Dipeptide Derivatives containing a Quinonyl Moiety via Aminoacyl Intermediates

概要

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3-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl) propanoic acid, 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl) decanoic acid, 6-(2,3,5-trimethyl-1,4-benzoquinon-6-yl)-hexanoic acid, 9-(2-methyl-1,4-naphthoquinon-3-yl) nonanoic acid were coupled to Nacetyl-6-O-aminoacylmuramyl-α-aminoisobutyryl-D-isoglutamines by the active ester method. The aminoacyl residues used were Gly, β-Ala, L-Pro, L-Leu, D-Leu, Ahx and Aud. Most of the resulting derivatives showed more potent adjuvant activity than N-acetyl-muramyl-L-alanyl-D-isoglutamine, an active constituent of mycobacterial cell wall peptidoglycan, for the induction of delayed-type hypersensitivity. The strength of the activity was affected by the combination of quinonyl acids and linking amino acids, and the present study indicated that the incorporation of an ω-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl) alkanoyl moiety through Leu was most favorable.
公益社団法人日本薬学会の論文
1981-08-25