N-Acetyl-muramyl-dipeptides

III. Synthesis of Other N-acetyl-muramyl-dipeptides, Analogues and Derivatives of... 

Azuma, I., K. SuGiMURA, T. Taniyama, M. Yamawaki, Y. Yamamura, S. Kusumoto, S. Okada, and T. Shiba Adjuvant activity of mycobacterial fractions immunological properties of synthetic N-acetyl-muramyl dipeptide and the related compounds. Infect. Immun. 14, 18 (1976). 

Masek, K., M. Zaoral, j. Jezek, and R. Straka Immunoadjuvant activity of synthetic N-acetyl-muramyl-dipeptide. Experientia 34, 1363 (1978). 

Azuma, I., K. Kamisango, I. Saiki, Y. Tanio, S. Kobayashi, and Y. Yamamura Adjuvant activity of N-acetyl-muramyl dipeptides for the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. Infect. Immun. 29, 1193 (1980). 

MDP muramyl dipeptide (N-acetyl-muramyl-L-alanyl-D-isoglutamine) WSA Water Soluble Adjuvant AL multi-poly-D, L-alanyl-poly-L-lysine... 

Further degradation of low molecular weight fractions obtained from lysozyme digestion of cell walls then led to the conclusion that an N-acyl muramyl dipeptide should be the minimal adjuvant active structure (small square frame of Fig. 2). And indeed, N-acetyl-muramyl-L-alanyl D-isoglutamine (1) first synthesized by Merser et al. (49, 50) was found to be fully active (16). Kotani et al. (29, 30) independently came to the same conclusion. 

The synthesis of N-acetyl-P-D-glucosaminyl-(l- 4)-N-acetyl-mur-amyl-dipeptide according to various synthetic (82—84) and hemi-synthetic (85) procedures has been described, and, also, the synthesis of one of its isomers 0-(N-acetyl-P-muramyl-L-alanyl-D-isoglutamine)-(l- 4)-N-acetyl-D-glucosamine (90) (86). 

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