Synthesis of altritol nucleoside phosphoramidites for oligonucleotide synthesis.
This unit describes in detail the optimized preparations of altritol nucleoside phosphoramidite building blocks for oligonucleotide synthesis (aA, aG, aC, aU). D-Altritol nucleosides with adenine and uracil bases are obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol using the 1,8-diazabicyclo[5.4.0]undec-7-ene salts of the above-mentioned salts, while phase transfer catalysis (18-crown-6, K2CO3) is optimal for alkylation of 2-amino-6-chloropurine. The cytosine nucleoside is synthesized starting from the uracil congener. The 3'-hydroxyl function of hexitol sugar is protected with the benzoyl group.
Abramov
Mikhail
M
Rega Institute for Medical Research, Leuven, Belgium.
Herdewijn
Piet
P
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis*; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013402:Sugar Alcohols / Q000737:chemistry
D000577:Amides; D009705:Nucleosides; D009841:Oligonucleotides; D010756:Phosphoric Acids; D013402:Sugar Alcohols; C042890:altritol; C011067:phosphoramidic acid