Biopolym. Cell. 1987; 3(6):294-301.
http://dx.doi.org/10.7124/bc.000200
Structure and Function of Biopolymers
Specificity of interaction of qlycine and its methyl derivatives with nucleic acid base from nuclear magnetic resonance data
1Bruskov V. I., 1Kutyshenko V. P.
  1. Institute of Biological Physics, Academy of Sciences of the USSR
    Pushchino, Moscow Region, USSR

Abstract

Interaction of glycine and its O- and N-methyl derivatives with nucleic acid bases have been investigated by the NMR method. O-methylglycine selectively interacts with cytosine and guanine in dirnethylsulphoxide (DMSO) solution. Cytosine forms a complex where NH+3-group of O-methylglycine specifically interacts with O2 and N3 atoms with simultaneous formation of hydrogen bonding between carbonyl group and NH2-group of cytosine. For guanine the complex formation is, probably, due to interaction of NH+ group with O6, N7 atoms and hydrogen bonding of carbonyl group with Nl-H-group. The methylglycine derivatives form complexes with cytosine and guanine and compete for hydrogen bonds formation in guanine-cytosine pairs in DMSO: H2O (3:1) solutions. But O-methylglycine forms a complex preferably with cytosine, whereas N-methylglycine — with guanine. The data obtained indicate the interaction of glycine with cytidine, CMP and GMP in water.
Full text: (PDF, in Russian)

References

[1] Helene C, Maurizot JC. Interactions of oligopeptides with nucleic acids. CRC Crit Rev Biochem. 1981;10(3):213-58.
[2] Helene C, Lancelot G. Interactions between functional groups in protein-nucleic acid associations. Prog Biophys Mol Biol. 1982;39(1):1-68.
[3] Smol'ianinova TI, Bruskov VI, Kashparova EV. Model studies of DNA-protein interaction. I. Effect of aminocarboxylic and amide groups of amino acids on DNA thermostability and conformation. Mol Biol (Mosk). 1985;19(4):992-1000.
[4] Smol'ianinova TI, Bruskov VI. About mechanism of interaction of DNA with glycine according to spectrophotometric thermal melting and circular dichroism: Proc. of reports. V All-Union conf. on spectroscopy of biopolymers. Kharkiv, 1984:213-5.
[5] Bruskou VI. Specificity of interaction of nucleic acid bases with hydrogen bond forming amino acids. Stu, biophys. 1978; 67(1):43-44.
[6] Bruskov VI, Bushuev VN. Study by the proton magnetic resonance method of complex formation between nucleosides and compounds modeling amino acid residues of proteins in dimethyl sulfoxide. Biofizika. 1977;22(1):26-31. Russian.
[7] Lancelot G, Helene C. Selective recognition of nucleic acids by proteins: the specificity of guanine interaction with carboxylate ions. Proc Natl Acad Sci U S A. 1977;74(11):4872-5.
[8] Lancelot G, Mayer R. The specific interactions of guanine with carboxylate ions in water. FEBS Lett. 1981;. 130(1):7-11.
[9] Greenstein JP, Winitz M. Chemistry of Amino Acids. New York; London, Wiley, 1961; 2872 p.
[10] Plaush AC, Sharp RR. Ion binding to nucleosides. A 35C1 and 7Li NMR study. J Am Chem Soc. 1976;98(25):7973-80.
[11] Rendell MS, Harlos JP, Rein R. Specificity in the genetic code. The role of nucleotide base-amino acid interaction. Biopolymers. 1971;10(11):2083-94.
[12] Gul'tiaev AP, Samoilenko SA, Zheltovskii NV. Spectroscopic study of interactions between nucleic acid bases and amino acid esters in dimethylsulfoxide. Mol Biol (Mosk). 1981;15(6):1295-302.
[13] Neurohr KJ, Mantsch HH. A proton NMR study of the intermolecular association of naturally occurring nucleotides in aqueous solution. Can J Spectrosc. 1980; 5(4):106-9.
[14] Raszka M. Mononucleotides in aqueous solution: proton magnetic resonance studies of amino groups. Biochemistry. 1974;13(22):4616-22.
[15] Pinnavaia TJ, Marshall CL, Mettler CM, Fisk CL, Miles HT, Becker ED. Alkali metal ion specificity in the solution ordering of a nucleotide, 5'-guanosine monophosphate. J Am Chem Soc. 1978; 100(11):3625-3629.
[16] Raszka M, Kaplan NO. Association by hydrogen bonding of mononucleotides in aqueous solution. Proc Natl Acad Sci U S A. 1972;69(8):2025-9.
[17] Young MA, Krugh TR. Proton magnetic resonance studies of double helical oligonucleotides. The effect of base sequence on the stability of deoxydinucleotide dimers. Biochemistry. 1975;14(22):4841-7.
[18] Krugh TR, Laing JW, Young MA. Hydrogen-bonded complexes of the ribodinucleoside monophosphates in aqueous solution. Proton magnetic resonance studies. Biochemistry. 1976;15(6):1224-8.