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Molecular interactions between electrophiles and nucleic acids. I—Raman spectroscopic study of the molecular reactivity of three typical methylating agents
Author(s) -
Bertoluzza A.,
Fagnano C.,
Morelli M. A.,
Tosi R.
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.1250180202
Subject(s) - chemistry , nucleic acid , electrophile , raman spectroscopy , reactivity (psychology) , methanol , aqueous solution , hydrolysis , carcinogen , derivative (finance) , medicinal chemistry , organic chemistry , stereochemistry , biochemistry , medicine , physics , alternative medicine , pathology , financial economics , optics , economics , catalysis
Three methylating agents with different carcinogenic powers, dimethyl sulphate [(CH 3 O) 2 SO 2 (DMS)], methyl methanesulphonate [CH 3 SO 2 OCH 3 (MMS)] and N ‐methyl‐ N ‐methyl‐ N ‐nitrosourea [CH 3 N(NO)CONH 2 (MNU)], were studied by Raman spectroscopy in order to identify the reactive species which are formed in buffered aqueous solution at neutral pH. In all cases, the formation of methanol was observed. By hydrolysis DMS produces CH 3 OSO 3 − , and H 3 O + ions, and MMS produces CH 3 SO 3 − and H 3 O + ions. In the case of MNU the reaction is more complex and proceeds with gaseous products to give methanol quantitatively. This investigation is a preliminary to the study of molecular interactions between the three methylating agents and nucleic acid components.