Synthesis of immunologically active muramyl dipeptide derivatives containing a quinonyl moiety via aminoacyl intermediates.
抄録
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.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 29 (8), 2215-2221, 1981
公益社団法人 日本薬学会