Premium
Molecular interactions between electrophiles and nucleic acids. II —Raman and infrared spectra of adenine, adenine hydrochloride and the corresponding 1‐methyl derivatives in relation to tautomerism and mutagenic phenomena of bases of nucleic acids
Author(s) -
Bertoluzza A.,
Fagnano C.,
Tosi R.,
Morelli M. A.,
Long D. A.
Publication year - 1987
Publication title -
journal of raman spectroscopy
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.748
H-Index - 110
eISSN - 1097-4555
pISSN - 0377-0486
DOI - 10.1002/jrs.1250180203
Subject(s) - tautomer , chemistry , hydrochloride , raman spectroscopy , electrophile , nucleic acid , nucleobase , hydrogen bond , stereochemistry , computational chemistry , medicinal chemistry , molecule , dna , organic chemistry , biochemistry , physics , optics , catalysis
The Raman and IR spectra of adenine (AH 3 ) and of its derivatives adenine hydrochloride (AH 4 Cl), 1‐methyladenine (1MeAH 2 ) and 1‐methyladenine hydrochloride (1MeAH 3 Cl) are discussed in relation to the mutagenic and carcinogenic activities that they display. The spectra give evidence for a shift of tautomeric stability from the aminic form, which is favoured in AH 3 , toward the iminic, or iminic‐derived form, in the derivatives AH 4 Cl, 1MeAH 2 and 1MeAH 3 Cl. The different biological activities of this series of compounds, in particular the mutagenic and carcinogenic effects, can be interpreted in terms of different reactivites associated with the π electronic systems, and of a hydrogen‐bond coupling different from the canonical Watson–Crick type.