Carboxylic acid functionalized cobalt(III) cyclen complexes for catalytic hydrolysis of phosphodiester bonds.
4-(1,4,7,10-Tetraazacyclotetradec-1-yl)methylbenzoic acid (cycmba, 1) has been synthesized, as a step towards the eventual development of sequence-specific hydrolytic complexes. A cobalt(III) complex of 1, [Co(cycmba)Cl2]Cl.1.5H2O (.1.5H2O) was found to be active against both an activated phosphodiester compound, bis(nitrophenyl)phosphate (BNPP), and supercoiled DNA. The presence of the benzoate group depresses the rate of hydrolysis of the ligand-Co(III) system at neutral pH, as confirmed by the kinetics results of a methyl ester analog. The ability of (2.1.5H2O) to bind to solid substrates and remain active was also demonstrated by attachment of the molecule to agarose beads.
Knight
D Andrew
DA
Department of Chemistry, Loyola University, 6363 St. Charles Avenue, New Orleans, LA 70118, USA. daknight@loyno.edu
Delehanty
James B
JB
Goldman
Ellen R
ER
Bongard
Jason
J
Streich
Frederick
F
Edwards
Laura W
LW
Chang
Eddie L
EL
D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000032:analysis / Q000737:chemistry; D003035:Cobalt / Q000737:chemistry*; D000080027:Cyclams; D004247:DNA / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008024:Ligands; D008863:Microspheres; D015394:Molecular Structure; D011199:Potentiometry; D012685:Sepharose; D013057:Spectrum Analysis; D014867:Water / Q000737:chemistry
D002264:Carboxylic Acids; D002712:Chlorides; D000080027:Cyclams; D006571:Heterocyclic Compounds; D008024:Ligands; D014867:Water; D003035:Cobalt; D004247:DNA; D012685:Sepharose; C038072:cyclen