Synthesis and characterization of 1,1,4,4-butanetetracarboxylic acid. A di-gamma-carboxyglutamic acid (GlaGla) analogue.
1,1,4,4-Butanetetracarboxylic acid (BTCA) is evaluated as an analogue for the metal binding site in dipeptides of gamma-carboxyglutamic acid (Gla). Molecular modeling suggests that the four carboxylic acid groups in BTCA can assume a similar conformation to the four gamma-carboxylic acid groups in GlaGla and thus provides the impetus for the synthesis and metal binding determinations. BTCA is synthesized via the tert.-butyl ester and characterized via NMR, mass spectroscopy, and elemental composition. Equilibrium binding constants with protons, Ca(II) and Mg(II) are determined via pH and Ca(II) ion-selective electrode titrations and are found to be similar to those for GlaGla peptides with blocked termini.
Department of Chemistry, University of North Carolina, Chapel Hill.
S E
SE
Cabaniss
K C
KC
Pugh
P S
PS
Charifson
L G
LG
Pedersen
R G
RG
Hiskey
D001665:Binding Sites; D002118:Calcium / Q000378:metabolism*; D002264:Carboxylic Acids / Q000378:metabolism*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D008274:Magnesium / Q000378:metabolism; D008958:Models, Molecular; D008968:Molecular Conformation
D002264:Carboxylic Acids; D004151:Dipeptides; C065777:1,1,4,4-butanetetracarboxylic acid; C014390:gamma-carboxyglutamyl-gamma-carboxyglutamic acid; D008274:Magnesium; D002118:Calcium