The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides.
The syntheses of the four novel, base protected 5'-(S-triphenylmethyl)mercapto-2',5'-dideoxyribonucleoside-3 '-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) are described. These compounds have been used to prepare 5'-(S-triphenylmethyl) mercapto-oligodeoxyribonucleotides, which are readily purified by reversed phase h.p.l.c., owing to the highly lipophilic trityl group. After cleavage of the S-trityl group by silver or mercuric ions, the free thiol moiety can be coupled to a wide variety of reagents, generating very useful probes. Fluorescent labelled 5'-mercapto-oligodeoxyribonucleotides are being used for automated DNA sequencing without radioactivity, and heavy metal labelled 5'-mercapto-oligonucleotides will be used in X-ray crystallography.
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000138:chemical synthesis; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction / Q000379:methods
D005456:Fluorescent Dyes; D009838:Oligodeoxyribonucleotides