Synthesis of neo-glycosylated L-alanyl-D-isoglutamine derivatives as potential immunoadjuvants.
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.
Siedler
F
F
Max-Planck-Institut für Biochemie, Martinsried.
Rudolph
S
S
Musiol
H J
HJ
Moroder
L
L
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives*; D000276:Adjuvants, Immunologic / Q000737:chemistry*; D005942:Gluconates / Q000737:chemistry; D005965:Glucuronates / Q000737:chemistry; D020723:Glucuronic Acid; D006020:Glycopeptides / Q000737:chemistry*; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry; D013400:Sugar Acids / Q000737:chemistry
D000276:Adjuvants, Immunologic; D005942:Gluconates; D005965:Glucuronates; D006020:Glycopeptides; D007783:Lactones; D013400:Sugar Acids; C015252:gulonic acid; D000119:Acetylmuramyl-Alanyl-Isoglutamine; D020723:Glucuronic Acid; C030691:gluconic acid