title: Synthesis of guanosine and deoxyguanosine phosphoramidites with cross-linkable thioalkyl tethers for direct incorporation into RNA and DNA.
abstract: We describe the synthesis of protected phosphoramidites of deoxyriboguanosine and guanosine derivatives containing a thiopropyl tether at the guanine N2 (7a,b) for site-specific crosslinking from the minor groove of either DNA or RNA to a thiol of a protein or another nucleic acid. The thiol is initially protected as a tert-butyl disulfide that is stable during oligonucleotide synthesis. While the completed oligonucleotide is still attached to the support, or after purification, the tert-butyl thiol can readily be removed or replaced by thioethylamine or 5-thio-2-nitrobenzoic acid, which have more favorable crosslinking rates.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
authors.forename: Xiaorong
authors.initials: X
authors.lastname: Hou
authors.forename: Gang
authors.initials: G
authors.lastname: Wang
authors.forename: Barbara L
authors.initials: BL
authors.lastname: Gaffney
authors.forename: Roger A
authors.initials: RA
authors.lastname: Jones
mesh_terms: D001483:Base Sequence; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D003849:Deoxyguanosine / Q000138:chemical synthesis / Q000737:chemistry*; D006151:Guanosine / Q000138:chemical synthesis / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012313:RNA / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D003432:Cross-Linking Reagents; D009943:Organophosphorus Compounds; D013438:Sulfhydryl Compounds; C434331:phosphoramidite; D006151:Guanosine; D012313:RNA; D004247:DNA; D003849:Deoxyguanosine