Synthesis and Immunoadjuvant Activity of 1-α-O-, 1-β-S- and 6-O-(2-Tetradecylhexadecanoyl) Derivatives ofN-Acetylmuramoyl-l-alanyl-d-isoglutamine Methyl Ester

The Legacy of Hideki Yukawa, Sin-itiro Tomonaga, and Shoichi Sakata: Some Aspects from their Archives

“…In 1937 three groups, S. H. Neddermeyer and C. D. Anderson [13]; Nishina, M. Takeuchi and T. Ichimiya [14,15]; J. C. Street and E. C. Stevenson [16], discovered a new particle with mass consistent with that of Yukawa's particle in the cosmic ray by cloud-chamber experiments. (Fig.3) to Yukawa at Osaka Imperial University for an informal discussion meeting on mesons among theoretical and cosmic-ray physicists [17].…”

Synthesis and Immunoadjuvant Activity of 1-α-O- and 1-β-S-[(3R)-3-Tetradecanoyloxytetradecanoyl]-N-acetylmuramoyl-L-alanyl-D-isoglutamine Methyl Esters and Related Compounds

“…methyl ester (3). A solution of 2 (409mg, 0.41 mmol) in 80% aqueous acetic acid (15 ml) was heated for 1 h at 45°C, and then concentrated to N- - (X-o-glucopyranos-3-yl (4).…”

“…In the continuous effort to obtain an efficient immunoadjuvant on the basis of the structure-activity relationship of MDP, it was demonstrated that I-f3-S-(2-tetradecylhexadecanoyl)-MDP methyl ester 3 ) greatly augmented the humoral antibody response and, …”