[Interaction of formaldehyde with nucleic acids and their structural components in the presence of amines. II. Structure of adenine derivatives formed in the reaction with formaldehyde and primary amine].
Two products of modified adenine have been isolated from reaction of adenine with a mixture of formaldehyde and methylamine; their structures have been demonstrated by UV, 1H NMR and mass spectra data. The formal scheme of reaction can be described as simultaneous or sequential cycloaddition of dimethylol derivatives of methylamine to two reaction's positions of the adenine residue. This results in the formation of a new partly or completely hydrogenated six-membered 1,3,5-triazine cycle which has the atoms of adenine nitrogen in its 1,3-positions and nitrogen of methylamine in 5-position. This is used as a model for discussing the peculiarities of DNA-formaldehyde interaction in the presence of amine.
D000225:Adenine / Q000031:analogs & derivatives*; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA; D005557:Formaldehyde; D006863:Hydrogen-Ion Concentration; D008744:Methylamines; D013056:Spectrophotometry, Ultraviolet
D008744:Methylamines; D005557:Formaldehyde; D004247:DNA; C027451:methylamine; D000225:Adenine
Vzaimodeĭstvie formal'degida s nukleinovymi kislotami i ikh strukturnymi komponentami v prisutstvii aminov. II. Stroenie proizvodnykh adenina, obrazuiushchikhsia pri reaktsii s formal'degidom i pervichnym aminom.