Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis and Immunoadjuvant Activity of Acylamino Analogs of N-Acetylmuramoyl-L-alanyl-D-isoglutamine
Hiroyuki OKUMURAKei-ichi KAMISANGOIkuo SAKIYoshiro TANIOIchiro AZUMAMakoto KISOAkira HASEGAWAYuichi YAMAMURA
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1982 年 46 巻 2 号 p. 507-514

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A variety of long-chain fatty acylamino analogs of N-acetylmuramoyl-L-alanyl-D-isoglutamine (MDP), such as N-(acyl)muramoyl-dipeptides (1) and N-acetyl-6-(acylamino)-6-deoxymuramoyl-dipeptides (2), were synthesized to examine their immunological activities. All the N-(acyl)muramoyl-L-alanyl-D-isoglutamines (1) were active as adjuvant on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. N-(3-Hydroxy-2-tetradecyloctadecanoylamino)muramoyl-L-alanyl-D-isoglutamine (1d) and N-acetyl-6-deoxy-6-(3-hydroxy-2-docosylhexacosanoylamino)murarnoyl-L-alanyl-, -L-valyl-, and -L-seryl-D-isoglutamines (2) showed antitumor activity by suppressing tumor (Meth-A fibrosarcoma) growth in syngeneic BALB/c mice.
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