The 4-methylthio-1-butyl group for phosphate/thiophosphate protection in oligodeoxyribonucleotide synthesis.
The detailed preparation of deoxyribonucleoside phosphoramidites functionalized with a 4-methylthio-1-butyl group for P(III) protection is described, along with the incorporation of these phosphoramidites into DNA oligonucleotides via solid-phase techniques. The versatility of the thermolabile 4-methylthio-1-butyl phosphate/thiophosphate-protecting group is exemplified through its facile removal from oligonucleotides under neutral conditions or under standard basic conditions. The sulfonium salt that is produced during the thermolytic deprotection of oligonucleotides did not alter DNA nucleobases or desulfurize phosphorothioate diesters to a significant extent.
Cieślak
Jacek
J
Food and Drug Administration, Bethesda, Maryland, USA.
Grajkowski
Andrzej
A
Livengood
Victor
V
Beaucage
Serge L
SL
D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*
D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D010710:Phosphates; C434331:phosphoramidite; C035638:thiophosphoric acid