Synthesis and immunological evaluation of the conjugates composed from a muramyl peptide GMDP and tuftsin.
The conjugates of a muramyl dipeptide analog GMDP (N-acetylglucosaminyl beta 1-->4 N-acetylmuramyl-L-alanyl-D-isoglutamine) and tuftsin (Thr-Lys-Pro-Arg) were synthesized from unprotected GMDP by mixed anhydride procedure. The identity of the conjugates was confirmed by high resolution NMR and their immunomodulating properties were determined in various tests. It was found that the conjugate in which the GMDP carboxyl group forms an amide bond with the epsilon-amino group of tuftsin lysyl residue exceeds GMDP in all the activities determined. Synergism of GMDP and tuftsin was found in phagocytosis stimulation assay.
Titov
V M
VM
Laboratory of Peptide Chemistry, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Moscow, Russia.
Meshcheryakova
E A
EA
Balashova
T A
TA
Andronova
T M
TM
Ivanov
V T
VT
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D000595:Amino Acid Sequence; D000818:Animals; D000917:Antibody Formation; D006168:Guinea Pigs; D006968:Hypersensitivity, Delayed / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008969:Molecular Sequence Data; D010047:Ovalbumin / Q000276:immunology; D010587:Phagocytosis; D014405:Tuftsin / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology*
D000119:Acetylmuramyl-Alanyl-Isoglutamine; C063429:glucosaminylmuramyl-2-alanine-D-isoglutamine; D010047:Ovalbumin; D014405:Tuftsin