Conformation and configuration at the central amine nitrogen of a nucleotide adduct of the carcinogen 2-(acetylamino)fluorene as studied by 13C and 15N NMR spectroscopy.
J Biomol Struct Dyn
; 3(5): 923-34, 1986 Apr.
Article
em En
| MEDLINE
| ID: mdl-3271418
ABSTRACT
The conformation and configuration at the central nitrogen of the adduct 8-(N-fluoren-2-ylamino)-2'-deoxyguanosine 5'-monophosphate has been investigated by high-field 13C and 15N NMR spectroscopy. One-bond nitrogen-hydrogen coupling constants and 13C chemical shifts for the adduct as well as for the model compounds diphenylamine, 4-nitrodiphenylamine and 2-aminofluorene have been measured in nonaqueous solutions. The data indicate a near planar configuration at the amine nitrogen that links the guanine and fluorene rings of the adduct. The orientations about the guanyl-nitrogen and fluorenyl-nitrogen bonds place the two ring systems in either perpendicular (Type A) or helical (Type B) conformations. It is suggested, based on structural similarities to diarylamines, that the G-N-C bond angle of the adduct is greater than 120 degrees in order to reduce unfavorable steric interactions between the two ring systems. Space-filling molecular models of the adduct in duplex DNA show that the aminofluorene moiety can be oriented into both Type A and Type B conformations within the major groove. The configuration at nitrogen of diphenylamine, 4-nitrodiphenylamine and 2-aminofluorene has also been examined.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
2-Acetilaminofluoreno
/
Nucleotídeos de Desoxiguanina
Idioma:
En
Revista:
J Biomol Struct Dyn
Ano de publicação:
1986
Tipo de documento:
Article