Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides.
Two classes of aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite to produce the corresponding polymer-bound phosphitylating reagents. These were reacted with a number of unprotected nucleosides and carbohydrates in the presence of 1H-tetrazole. Oxidation with tert-butyl hydroperoxide followed by removal of the cyanoethoxy group with 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the corresponding polymer-bound phosphate diesters. Acidic cleavage of the p-acetoxybenzyl alcohol linker yielded monophosphorylated products with high regioselectivity and trapped linkers on the resins that can be reused.
Ahmadibeni
Yousef
Y
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, The University of Rhode Island, Kingston, RI 02881, USA.
Parang
Keykavous
K
D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000737:chemistry*; D007202:Indicators and Reagents; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism; D010766:Phosphorylation
D002241:Carbohydrates; D007202:Indicators and Reagents; D009705:Nucleosides