title: Synthesis and stereoselective DNA binding abilities of new optically active open-chain polyamines.
abstract: The efficient synthesis of new open-chain enantiopure polyamines bearing (R,R)- and/or (S,S)-trans-cyclohexane-1,2-diamine moieties is described. The key step for the synthetic procedure is the selective monoalkylation of the cyclohexanebis(sulfonamide) core, which allows the subsequent functionalization of this moiety. Compounds bearing different combinations of absolute configurations, length of the aliphatic spacers and terminal groups have been prepared. As a demonstration of the potential utility of the obtained compounds, the preliminary DNA binding abilities of some of them have been studied by UV-measurements of melting temperatures (Tm). The effects of the absolute configuration of the corresponding chiral centers and the length of the spacer separating the cyclohexanediamine moieties on the strength of the interaction with DNA are also discussed.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain.
authors.forename: Carmen
authors.initials: C
authors.lastname: Peña
authors.forename: Ignacio
authors.initials: I
authors.lastname: Alfonso
authors.forename: Blake
authors.initials: B
authors.lastname: Tooth
authors.forename: Nicolas H
authors.initials: NH
authors.lastname: Voelcker
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
mesh_terms: D000478:Alkylation; D001665:Binding Sites; D003514:Cyclohexylamines; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D009691:Nucleic Acid Denaturation; D011073:Polyamines / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature
chemical_list: D003514:Cyclohexylamines; D011073:Polyamines; D004247:DNA