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Correlation of structure and adjuvant activity of n acetylmuramyl l alanyl s iso glutamine its derivatives and analogs anti adjuvant and competition properties of stereo isomers



Correlation of structure and adjuvant activity of n acetylmuramyl l alanyl s iso glutamine its derivatives and analogs anti adjuvant and competition properties of stereo isomers



Biochemical and Biophysical Research Communications 72(1): 339-346



Synthetic MDP was previously shown to be fully adjuvant active in a water-in-oil emulsion; this paper reports the adjuvant activity [in guinea pigs] of 10 derivatives and analogs of MDP under similar conditions. NaBH4 reduction of MDP leads to the inactive muramicitol dipeptide; .beta.-elimination gives the lactyl-dipeptide, which seems to inhibit adjuvant activity. Shortening of the lactyl side chain of MDP gives nor-MDP, which is less active. Among the analogs in which 1 amino acid of the dipeptide moiety is replaced by another one, the L-Ser analog is fully active, whereas replacement of L-Ala by Gly or of D-iso-Gln by D-Glu-OH, D-Glu (OMe)2 [D-Glu(OCH3)2] or D-Glu (OMe)-NH2 gives less active compounds. The diastereoisomer where L-Ala is replaced by D-Ala, shows an anti-adjuvant activity.

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Accession: 005061457

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