NUCLEOSIDE COMPLEXING - RAMAN AND C-13 NMR SPECTROSCOPIC STUDY OF THE BINDING OF HARD AND SOFT METAL SPECIES

• Type: Article in International Scientific Journal
• Date: 1980

Authors

MARZILLI, LG (Author) Other; DECASTRO, B (Author) FEUP; CARADONNA, JP (Author) Other; STEWART, RC (Author) Other; VANVUUREN, CP (Author) Other

Journal

Title: Journal of the American Chemical Society

Vol. 102

Pages: 916-924

ISSN: 0002-7863

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 76 Citations

Scopus - 43 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-005-6GY

DOI: 10.1021/ja00523a004

Abstract (EN): The influence of a wide variety of metal salts and complexes on the Raman and 13C NMR spectra of three of the four common nucleosides (uridine, adenosine, and cytidine) in Me2SO has been determined. Several related molecules also studied included deoxycytidine, 5-methyldeoxycytidine, 8-bromoadenosine, 6-dimethylaminopurine-9-riboside, and N4,N4-dimethyl-amino-1-methylcytosine. Inorganic species utilized included cis-[Pt(Me2SO)2Cl2], HgCl2, Zn(NO3)2, Cd(NO3,)2, Pb(NO3)2, Pb(ClO4)2, PbCl2, Mg(NO3)2, Ca(NO3)2, Sr(NO3)2, Ba(NO3)2, BaCl2, La(NO3)3, Pr(NO3)3, Lu(NO3)3, Lu(ClO4)3, Ga(NO3)3, LiClO4, NEt4Cl, and NEt4NO3. The 13C NMR shift dependencies on metal concentration were used to calculate formation constants for selected purine and pyrimidine derivatives. Constants obtained with HgCl2 agreed well with literature values. However, our studies suggest that alkaline earth metal ions have a lower affinity for nucleosides than that suggested previously. Of the common nucleosides, cytidine has the greatest affinity for alkaline earth metal ions and these appear to bind to O-2. Raman and 13C NMR studies with N4,N4-dimethylamino-1-methylcytosine are presented which support the O-2 binding mode. The only electrophile capable of interacting with N-3 of this pyrimidine is the H+ ion. Conclusions drawn about binding sites to other nucleosides are in agreement with previous studies. A summary table specifying the importance of anion and cation binding to the four common nucleosides is included. This summary provides a rationale for all of the literature observations and should help to minimize the confusion currently surrounding the nature of the interactions of inorganic species with nucleosides in Me2SO. © 1980 American Chemical Society.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9