Synthesis of neo-glycosylated L-alanyl-D-isoglutamine derivatives as potential immunoadjuvants
Siedler, F.; Rudolph, S.; Musiol, H.J.; Moroder, L.
Peptide Research 5(1): 39-47
1992
ISSN/ISBN: 1040-5704 PMID: 1623302 Document Number: 400156
The synthesis is described for muramyl-dipeptide-related amphiphilic analogs, where 1,10-diaminodecane served as a lipophilic C-terminal linker for the preparation of a bidentated L-alanyl-D-isoglutamine derivative and incorporation of aldonic and uronic acids at the N-termini as hydrophilic cores. For the N-acylation steps via lactones, suitable conditions were elaborated to allow for the use of unprotected or minimally protected aldonic and uronic acid lactones, respectively. These procedures may represent a useful general approach for the synthesis of neoglycopeptides.