New syntheses of N-(guanosin-8-yl)-4-aminobiphenyl and its 5'-monophosphate.
N-Acetoxy-4-trifluoroacetylaminobiphenyl (N-acetoxy-TFAABP) reacted readily with Guo and GMP at neutrality in a one-step fashion to yield N-(guanosin-8-yl)4-aminobiphenyl (Guo-ABP) (I) and N(guanosin-8-yl)-4-aminobiphenyl-5'-monophosphate (GMP-ABP) (II), respectively. GMP-ABP could also be formed in much lower yield from the reaction of N-acetoxy-4-formylaminobiphenyl (N-acetoxy-FABP) with GMP (pH 7.0) under more rigorous conditions. Enzymatic hydrolysis of GMP-ABP with alkaline phosphatase in Tris buffer (pH 8.0) at 37 degrees C yielded Guo-ABP. Guo-ABP showed a brilliant blue fluorescence on exposure to 366 nm UV light and its UV absorption spectrum was identical to that of Guo-ABP prepared by Kriek via a different route. Elemental analysis and nuclear magnetic resonance (NMR) data further confirmed the identity of this compound.
D000611:Aminobiphenyl Compounds / Q000138:chemical synthesis* / Q000302:isolation & purification; D006150:Guanine Nucleotides; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D006157:Guanosine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet
D000611:Aminobiphenyl Compounds; D006150:Guanine Nucleotides; D006151:Guanosine; C028578:N-(guanosin-8-yl)-4-aminobiphenyl; C028579:N-(guanosin-8-yl)-4-aminobiphenyl-5'-monophosphate; D006157:Guanosine Monophosphate