ABSTRACT
Reductive amination of 3',5'-O-(tetraisopropyldisilyloxane-1,3-diyl)-2'-deoxy-5-formyluridine with several aliphatic and aromatic amines, in various solvents, is described. In the case of aliphatic amines, the expected C-5 substituted methylamino pyrimidine nucleosides are formed along with by-products deriving from opening of the pyrimidine ring. Relative amounts of the by-products depend upon the polarity of the solvent employed.
Subject(s)
Amines/chemistry , Deoxyuridine/analogs & derivatives , Deoxyuridine/chemical synthesis , Nucleosides/chemical synthesis , Magnetic Resonance Spectroscopy , Models, ChemicalSubject(s)
Amino Acid Transport System X-AG , Aspartic Acid/chemical synthesis , Carrier Proteins/chemistry , Glutamates/chemical synthesis , Sodium/metabolism , Symporters , Animals , Aspartic Acid/chemistry , Aspartic Acid/metabolism , Biological Transport , Carrier Proteins/metabolism , Cerebral Cortex/metabolism , Drug Design , Excitatory Amino Acid Transporter 3 , Glutamate Plasma Membrane Transport Proteins , Glutamates/chemistry , Glutamates/metabolism , In Vitro Techniques , Models, Molecular , Molecular Conformation , Neuroprotective Agents/chemical synthesis , Neuroprotective Agents/chemistry , Neuroprotective Agents/metabolism , Patch-Clamp Techniques , Radioligand Assay , Rats , Structure-Activity RelationshipABSTRACT
2'-Deoxy-8-(propyn-1-yl)adenosine has been incorporated in synthetic oligodeoxyribonucleotides and its influence on thermal stability of duplex and quadruplex structures investigated by UV, CD and 1H NMR. The obtained results seem to indicate that the presence of the modified base negatively affects the stability of double stranded DNA whereas remarkably increases the stability of parallel quadruplex structures.