2'-Hydroxyl-protecting groups that are either photochemically labile or sensitive to fluoride ions.
Protected ribonucleotide monomers are more difficult to obtain than their 2'-deoxy counterparts because of the need to protect the 2'-hydroxy function. This unit describes the stepwise preparation of suitably 2'-protected ribonucleosides using two protecting groups: 2-nitrobenzyloxymethyl (NBOM) and tert-butyldimethylsilyl (TBDMS). In addition, details are given for protecting the 5'-hydroxyl and the nucleobase, yielding nucleosides that are easily converted to phosphoramidite or H-phosphonate derivatives for automated oligoribonucleotide synthesis.
Miller
T J
TJ
Purdue University, West Lafayette, Indiana, USA.
Schwartz
M E
ME
Gough
G R
GR
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001671:Biochemistry / Q000379:methods*; D002845:Chromatography; D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D012263:Ribonucleosides / Q000138:chemical synthesis / Q000737:chemistry; D014320:Triphenylmethyl Compounds / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D012263:Ribonucleosides; D014320:Triphenylmethyl Compounds; D006151:Guanosine; D017665:Hydroxyl Radical; D003562:Cytidine; D000241:Adenosine; D005459:Fluorides; D014529:Uridine