Nucleic Acids Research · 1988 · 72 citations · 17 references
Life SciencesBiochemistryMolecular BiologyBiocatalysisBioorthogonal ChemistryNucleic Acid BiochemistryDisulfide Bond FormationDna LigationNucleic Acid CleavageNucleic Acid SynthesisOligonucleotide ChemistryChemical Modification Of OligonucleotidesDisulfide Bond ChemistryDisulfide Bond MispairingNon-native Disulfide Bond FormationOligonucleotide Cleavage ChemistryOligonucleotide Coupling ReactionsOligonucleotide LigationPhosphoramidate Oligonucleotides
We have developed general methods for joining together, via cleavable disulfide bonds, either two unprotected polynucleotides or a polynucleotide and a peptide or protein. To join two oligonucleotides, each is first converted to an adduct in which cystamine is joined to the 5'-terminal phosphate of the oligonucleotide by a phosphoramidate bond. The adducts are mixed and reduced with dithiothreitol. The dithiothreitol is then removed by dialysis. Oxidation by atmospheric oxygen occurs to yield the required dimer. To join an oligonucleotide to a cysteine-containing peptide or protein, the 5'-cystamine oligomer is first converted to a 2'-pyridyldisulfide adduct and then reacted with an excess of the peptide or protein. If the peptide does not contain a free cysteine residue, it is first treated with iminothiolane to introduce one or more sulfhydryl groups. We have used these procedures to join a 16 mer deoxynucleotide probe and MDV-1 RNA, a substrate of Q beta RNA polymerase. This adduct hybridizes with a complementary target DNA. We have also joined a 16mer probe to peroxidase and MDV-1 RNA to human IgG. The probe-peroxidase adduct maintains enzymatic activity and the MDV-1 RNA-IgG adduct binds to a complementary anti-IgG.
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George L. Ellman · Archives of Biochemistry and Biophysics · 1959 · 26.2K citations
Victor C. W. Tsang, José Mauro Peralta, Adrian Simons · Methods in enzymology on CD-ROM/Methods in enzymology · 1983 · 677 citations
Derivatization of unprotected polynucleotides
Barbara C.F. Chu, Geoffrey M. Wahl, Leslie E. Orgel · Nucleic Acids Research · 1983 · 182 citations · Full text