21064-69-7Relevant academic research and scientific papers
An effective reagent to functionalize alcohols with phosphocholine
Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.
supporting information, p. 767 - 770 (2020/02/11)
Phosphocholine is a small haptenic molecule that is both a precursor and degradation product of choline. Phosphocholine decorates a number of biologics such as lipids and oligosaccharides. In this study, an air and bench stable phosphocholine donor has been developed and evaluated with a number of alcohol acceptors. Using a one-pot, three-step sequence, (phosphitylation, oxidation, and phosphate deprotection) phosphocholine derivatives are synthesized in high yields. Of particular interest is the synthesis of miltefosine, the lone oral drug approved to treat leishmaniasis. Due to its prohibitive expense ($1500 per g), miltefosine is not accesable for the majority of the world's patients. Based on the described reaction sequence, this drug can be produced for $25 per g.
Facile reduction in the synthesis of phosphorylcholine affinity columns
Martin, Lenore M.
, p. 7921 - 7924 (2007/10/03)
Reduction of p-nitrophenylphosphorylcholine to the amine utilizing ammonium formate and 10% Pd/C in methanol, followed by in situ generation of the diazonium salt resulted in the synthesis of p-diazophenylphosphorylcholine. This reaction was simpler than the usual approach utilizing hydrogen gas for the reduction to p-aminophenylphosphorylcholine. The diazonium salt then successfully reacted with the amino acid tyrosine, which had been previously attached to an agarose bead. Alternatively the diazonium salt was coupled to BSA and the resulting conjugate used to coat ELISA plates. Selective PC-binding antibodies recognized the antigen, and bound specifically to both the column and plates.
