Cleavage of the phosphodiester bond of uridylyl-(3',5')-8-carboxymethylaminoadenosine by hydronium, hydroxide and zinc(II) ions: a model study aimed at elucidating the potential of a carboxylate function as an intramolecular catalyst.
Uridylyl-(3',5')-8-carboxymethylaminoadenosine has been synthesised, and its transesterification to uridine 2',3'-cyclic phosphate in the presence and absence of Zn2+ ion has been studied. The results show that a carboxylate function in the vicinity of the phosphodiester bond accelerates the metal ion promoted cleavage but not the metal ion independent reaction. Under acidic conditions, the predominant reaction is the cleavage of the side chain, giving the 8-amino derivative.
Mikkola
S
S
Department of Chemistry, University of Turku, Finland. satu.mikkola@utu.fi
Oivanen
M
M
Neuvonen
K
K
Piitari
S
S
Ketomäki
K
K
Lönnberg
H
H
D002384:Catalysis; D015226:Dinucleoside Phosphates / Q000737:chemistry*; D004952:Esters; D006868:Hydrolysis; D006878:Hydroxides / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009861:Onium Compounds / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D015032:Zinc / Q000737:chemistry*
D015226:Dinucleoside Phosphates; D004952:Esters; D006878:Hydroxides; D009861:Onium Compounds; C423484:uridylyl-(3',5')-8-carboxymethylaminoadenosine; C027727:hydronium ion; D015032:Zinc