Polyhydroxylated sapphyrins: multisite non-metallic catalysts for activated phosphodiester hydrolysis.
Enhanced hydrolysis rates for the cleavage of bis(4-nitrophenyl)phosphate (BNPP), a model phosphodiester, may be achieved by using appropriately designed ditopic receptors containing the known phosphate-binding nucleus, sapphyrin, attached covalently to suitably oriented polyhydroxyl subunits. Evidence for the interaction between sapphyrin and BNPP comes from solid-state X-ray diffraction analysis of a diprotonated dihydroxylated sapphyrin-BNPP complex and from solution-phase (31)P NMR spectroscopic binding studies. The sapphyrins described in this paper may have a role to play as oligonucleotide cleavage agents.
Král
Vladimír
V
Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Czech Republic. kral@vscht.cz
Lang
Kamil
K
Králová
Jarmila
J
Dvorák
Michal
M
Martásek
Pavel
P
Chin
Aileen O
AO
Andrievsky
Andrei
A
Lynch
Vincent
V
Sessler
Jonathan L
JL
D002384:Catalysis; D006860:Hydrogen Bonding; D006868:Hydrolysis; D006900:Hydroxylation; D007700:Kinetics; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*; D014961:X-Ray Diffraction
D009596:Nitrophenols; D011166:Porphyrins; C440448:sapphyrin; C002887:bis(4-nitrophenyl)phosphate