title: DNA interstrand cross-link formation using furan as a masked reactive aldehyde.
abstract: 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.
authors: Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan, Ghent, Belgium.
authors: Lieselot L G
authors: LLG
authors: Carrette
authors: Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan, Ghent, Belgium.
authors: Ellen
authors: E
authors: Gyssels
authors: Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan, Ghent, Belgium.
authors: Annemieke
authors: A
authors: Madder
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D003432:Cross-Linking Reagents; D005663:Furans; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; C039281:furan
keywords: cross-linking; furan; nucleoside; oligonucleotide