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Synthesis and biological activity of n acetylmuramyl l alanyl d iso glutamine analogs



Synthesis and biological activity of n acetylmuramyl l alanyl d iso glutamine analogs



Research Bulletin of the Faculty of Agriculture Gifu University (42): 169-176



Synthesis of some N-acetylmuramyl-L-alanyl-D-isoglutamine analogs was described and their immunoadjuvant activities were investigated. Reaction of cyclohexanol with L-2-chloropropionic acid in the presence of NaH afforded D-2-cyclohexyloxypropionic acid (2). Condensation of 2 with L-alanyl-D-isoglutamine benzyl ester with dicyclohexylcarbodiimide-N-hydroxysuccinimide, followed by hydrogenolysis with Pd-C catalyst (10%) gave D-2-cyclohexyloxypropionyl-L-alanyl-D-isoglutamine. DL-(1,3/2)-1-Acetamido-2-O- (D-2-propionyl-L-alanyl-D-isoglutamine)cyclohexanediol and its configurational isomer were synthesized from DL-(1,3/2)-1-acetamido-3-O-benzylcyclohexanediol and its stereoisomeric analog in a similar manner. Evidence in support of the structure assigned to these new derivatives is presented.

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Accession: 006561289

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