title: Design, synthesis, and incorporation of fluorous 5-methylcytosines into oligonucleotides.
abstract: A palladium-catalyzed Negishi coupling reaction has been developed to synthesize fluorous 5-methylcytosines. These fluorous nucleosides are incorporated into the oligonucleotides that correspond to part of the promoter region of Oct4, a master gene that undergoes dynamic DNA demethylation during cellular reprogramming. The separation of the fluorous oligonucleotides from its nonfluorous analogues has been achieved through solid-phase extraction over fluorous silica, suggesting its potential use in probing DNA demethylation.
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
authors.forename: Zhiquan
authors.initials: Z
authors.lastname: Song
authors.forename: Qisheng
authors.initials: Q
authors.lastname: Zhang
mesh_terms: D044503:5-Methylcytosine / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D002853:Chromatography, Liquid; D004247:DNA / Q000737:chemistry*; D019175:DNA Methylation; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D006801:Humans; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015335:Molecular Probes / Q000138:chemical synthesis*; D050814:Octamer Transcription Factor-3 / Q000235:genetics; D009841:Oligonucleotides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011401:Promoter Regions, Genetic; D012822:Silicon Dioxide / Q000737:chemistry; D052616:Solid Phase Extraction
chemical_list: D015335:Molecular Probes; D050814:Octamer Transcription Factor-3; D009841:Oligonucleotides; C494173:POU5F1 protein, human; D005461:Fluorine; D010165:Palladium; D044503:5-Methylcytosine; D012822:Silicon Dioxide; D004247:DNA