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Chemical synthesis and adjuvant activity of n acetylmuramyl l alanyl d iso glutamine analogs



Chemical synthesis and adjuvant activity of n acetylmuramyl l alanyl d iso glutamine analogs



Chemical & Pharmaceutical Bulletin (Tokyo) 29(6): 1644-1654



Twenty-two kinds of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) analogs were synthesized and their adjuvant activity on the induction of delayed-type hypersensitivity to ABA [N-acetyl-3(4-arsonophenylazo)]-N-acetyl-L-tyrosine was examined [in guinea pigs]. The L-alanine residue of MDP could be replaced with certain other amino acid residues without loss of activity. The structure-activity relationship of the compounds is discussed. With respect to replacement of the L-alanine residue of MDP in connection with adjuvant activity, it was shown that amino acids having a suitable side chain were effective, basic amino acids were unfavorable, aromatic amino acids were unfavorable, and acidic amino acids were effective. The D-isoglutamine residue of MDP was essential for the adjuvant activity. The adjuvant activity was decreased by esterification with methanol of the D-glutamic acid residue of MDP and related N-acetylmuramyldipeptides, but the adjuvant activity of D-glutamic acid diamide analogs was similar to that of MDP and its analogs.

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Accession: 004939613

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