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Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides.

Uddin MJ, Schulte MI, Maddukuri L, Harp J, Marnett LJ
Nucleosides Nucleotides Nucleic Acids. 2010 29 (11): 831-40

PMID: 21128170 · PMCID: PMC3019237 · DOI:10.1080/15257770.2010.530332

An efficient enzymatic synthesis of 6-chloropurine-2'-deoxyriboside from the reaction of 6-chloropurine with 2'-deoxycytidine catalyzed by nucleoside-2'-deoxyribosyltransferase (E.C. followed by chemical conversion into the 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino) phosphoramidite derivative is described. The phosphoramidite derivative was incorporated site-specifically into an oligonucleotide and used for the introduction of a tethered tetramethylrhodamine-cadaverine conjugate. The availability of an efficient route to 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite enables the facile synthesis of oligonucleotides containing a range of functional groups tethered to deoxyadenosine residues.

MeSH Terms (16)

Cadaverine Chromatography, Gel Chromatography, High Pressure Liquid Crystallography Fluorescent Dyes Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Nucleic Acid Conformation Oligonucleotides Organophosphorus Compounds Pentosyltransferases Purine Nucleosides Purines Rhodamines Spectrometry, Fluorescence

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