14093-45-9Relevant academic research and scientific papers
An effective reagent to functionalize alcohols with phosphocholine
Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.
, p. 767 - 770 (2020)
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.
Hydrogen bonding. Part 55. IR and thermodynamic study of the lower hydrates of phenylphosphorylcholine and methylphosphorylcholine
Akin, Anne C.,Harmon, Kenneth M.
, p. 55 - 64 (1994)
We have prepared phenylphosphorylcholine and methylphosphorylcholine as small, zwitterionic, H2O soluble analogs of the head groups of phosphatidylcholine molecules, and carried out IR and equilibrium vapor pressure studies on them.Phenylphosphorylcholine forms hydrates containing 2.5, 1.5 and 0.5 mol H2O, and methylphosphorylcholine forms hydrates with 2.5 and 0.5 mol H2O.There is some IR evidence for hydrogen bonding from H2O to the phenyl or methyl substituted oxygens of the phosphate goups, but the effect is slight.Hydrogen bonds in these hydrates do not differ appreciably from values for H2O or ice.Of the five hydrates, only methylphosphorylcholine hemihydrate bonds H2O tightly; however, there is no indication of strong hydrogen bonding in this compound.We conclude that the tenacious retention of the last molecule of H2O by phosphatidylcholine membranes does not arise fom hydrogen bonding between H2O and phosphate oxygen.
A NEW EFFICIENT AND VERSATILE SYNTHESIS OF ALKYL PHOSPHORYLCHOLINES
Magolda, R. L.,Johnson, P. R.
, p. 1167 - 1170 (2007/10/02)
A short and general synthetic method is described for the preparation of new phosphorylcholines.
