phosphoramidite and furan

This unit describes a method for interstrand cross-linking between a furan-modified oligonucleotide and its unmodified complement. The synthesis of two furan-modified phosphoramidites, selected based on high cross-linking yield versus improved cross-linking selectivity, is described. The methods allow gram-scale synthesis starting from stable and readily available furan derivatives. Cross-linking requires selective oxidation of the furan moiety to an aldehyde. The masked nature of the latter avoids undesired and off-target reactions, resulting in clean and high-yield cross-link formation.

Topics: Aldehydes; Chemistry Techniques, Synthetic; Cross-Linking Reagents; DNA; Furans; Oligodeoxyribonucleotides; Organophosphorus Compounds; Oxidation-Reduction

A novel furan containing phosphoramidite was synthesized and incorporated into model oligonucleotides. This glycol nucleic acid based building block contains a furan unit substituting the natural base, and can be used for post synthetic oligonucleotide modifications by orthogonal chemistries such as Schiff base formation after in situ oxidation or Diels-Alder cycloadditions.

Topics: Base Sequence; Furans; Nucleosides; Oligonucleotides; Organophosphorus Compounds

A variety of furan-modified nucleoside phosphoramidite monomers has been prepared and efficiently incorporated into oligonucleotides. These take part in Diels-Alder reactions with fluorescent maleimides to give fluorescent-labeled oligonucleotides. This represents a strategy for oligonucleotide labeling that is orthogonal to amine-based methods.

Topics: Amines; Deoxycytidine; Fluorescent Dyes; Furans; Hydrogen-Ion Concentration; Macromolecular Substances; Models, Chemical; Molecular Biology; Nucleosides; Nucleotides; Oligodeoxyribonucleotides; Oligonucleotides; Organophosphorus Compounds; Temperature