134785-37-8Relevant articles and documents
Macrocyclic Polyamines -N3 and -N4: Synthesis and Study of their ATP Complexation by 31P Nuclear Magnetic Resonance Spectroscopy
Prakash, T. P.,Pattuparanbil, Rajamohanan,Ganesh, Wagappa K.
, p. 1273 - 1278 (2007/10/02)
The macrocyclic polyamines -N3, compound 1, and -N4, compound 2, possessing a hydroxymethyl side-chain have been synthesized.The macrocyclisation was achieved by condensation of lysine ditosate 3b with appropriate components 5 and 6 in the presence of CsCO3 to obtain 7 and 8 in 33 and 37percent yield, respectively.The complexation of polyamines 1 and 2 with ATP was studied by 31P NMR spectroscopy, which indicated a specific recognition of γ-phosphorus of ATP (NMe4 salt) by the polyamines.The binding constant estimates indicated that ATP binds compound 2 ca. 35-times stronger than it does compound 1.The binding curves indicated a definite 1:1 stoicheiometry for 2:ATP complex, and not so well defined stoicheiometry for 1:ATP binding.The mononucleotides, AMP and cAMP, and dinucleotide TpT did not show significant complexation with either compound 1 or 2.The binding of ATP by macrocyclic polyamines 1 and 2 and the presence of a hydroxymethyl side-chain to link with a nucleophile may aid rational design of chemical nucleases.