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Phosphorylation of Amino Alcohols by Inorganic cyclo -Triphosphate

The phosphorylation of amino alcohols has been achieved using cyclo-triphosphate (P3m) in aqueous solution with their maximum yields of more than 98%. The products were imidotriphosphates1 of 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol, which were all stable. The reaction of 1-amino-2-propanol (1A2P) with P3m produced its triphosphate derivative. Its yield increased with the reaction time to reach a maximum of 96% after 8 h, and then decreased gradually. The triphosphate derivative of 1A2P decomposed to two monophosphate derivatives via a cyclic phosphate (Scheme 1). Similar to 1A2P, the phosphorylation of 2-aminoethanol and 1-amino-2-butanol proceeded with the same mechanism. These imidotriphosphates were unstable and gradually decomposed to monophosphates because of the vicinal OH group.