Synthesis of fluorescent muramyl dipeptide congeners. 2.
Muramyl dipeptide (MDP) analogues were prepared and utilized in the synthesis of new fluorescently labeled MDP derivatives for use as biologic probes. Thus, N alpha-(N-acetylmuramyl)-L-lysyl-D-isoglutamine (Lys-MDP, 4) and N alpha-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl)-L-lysine [MTP, 5] were synthesized and then reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to yield the fluorescent adducts, DTAF-Lys-MDP (6) and DTAF-MTP (7). The adjuvant activity of the fluorescent MDP derivatives was determined by the ability of the compounds to promote delayed skin test responses in guinea pigs immunized with ovalbumin (OA) and by evaluating the anti-OA activity of these guinea pigs.
Hiebert
C K
CK
Department of Internal Medicine, College of Medicine, University of Iowa, Iowa City 52242.
Kopp
W C
WC
Richerson
H B
HB
Barfknecht
C F
CF
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000138:chemical synthesis*; D000818:Animals; D004797:Enzyme-Linked Immunosorbent Assay; D005260:Female; D005456:Fluorescent Dyes; D006168:Guinea Pigs; D012882:Skin Tests
D005456:Fluorescent Dyes; D000119:Acetylmuramyl-Alanyl-Isoglutamine