Selective recognition of nucleic acids by proteins: the specificity of guanine interaction with carboxylate ions.
The interaction of carboxylate ions (acetate, butyrate) with nucleic aicd bases and nucleosides has been investigated by proton magnetic resonance in dimethyl sulfoxide (d6)/H2O mixtures. Carboxylate ions interacted only with guanine derivatives and led to a large downfield shift of the NH2 resonance. A 1:1 stoichiometry was deduced from a study of the concentration dependence of chemical shifts. A study of substituted guanine showed that hydrogen bonding involved N(1)H and NH2(2). An association constant of 110 M-1 was determined. This value is about 30 times higher than the association constant for guanine-cytosine base pair formation under the same experimental conditions. As a matter of fact, carboxylate ions induced a dissociation of guanine-cytosine base pairs. This guanine-carboxylate association is experimental evidence for a highly specific interaction that could play an important role in protein/nucleic acid recognition.
D000085:Acetates; D001665:Binding Sites; D002264:Carboxylic Acids; D055598:Chemical Phenomena; D002621:Chemistry; D003596:Cytosine; D006147:Guanine; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy
D000085:Acetates; D002264:Carboxylic Acids; D006147:Guanine; D003596:Cytosine
J Am Chem Soc. 1968 Sep 11;90(19):5069-74
5670795
Biochemistry. 1974 Feb 12;13(4):714-23
4855765
Proc Natl Acad Sci U S A. 1974 Aug;71(8):3185-8
4528733
Proc Natl Acad Sci U S A. 1976 Mar;73(3):804-8
1062791
J Am Chem Soc. 1974 May 29;96(11):3656-7
4833723
Biochemistry. 1975 Feb 11;14(3):558-63
234245
FEBS Lett. 1973 Mar 1;30(2):219-224
11947097
Biochemistry. 1974 Feb 12;13(4):724-30
4855766
J Biol Chem. 1967 Oct 25;242(20):4682-90
6061414
FEBS Lett. 1975 Oct 15;58(1):106-11
773680
FEBS Lett. 1977 Feb 15;74(1):10-3
838065
J Biol Chem. 1977 Jan 10;252(1):244-9
556724
Biophys J. 1977 Mar;17(3):243-54
843583
Mol Biol (Mosk). 1975 Mar-Apr;9(2):304-9
1219386
Nucleic Acids Res. 1975 Jun;2(6):961-9
1144068
J Am Chem Soc. 1976 Dec 8;98(25):7973-80
993512
J Am Chem Soc. 1968 Aug 28;90(18):5010-7
5665545
Biochimie. 1977;59(7):587-96
922051