Evidence map›Paper›PMID 31912847›Full record

ArticleOrganic & biomolecular chemistry2020

An effective reagent to functionalize alcohols with phosphocholine.

Lianyan L Xu, Lawrence J Berg, D Jamin Keith, Steven D Townsend

Open access · greenAbstract read
In one paragraph

Article in Organic & biomolecular chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
0.6field-weighted citation impact, top 32% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

6 citing papers in PubMed, 12 citations in OpenAlex.

  1. Review
  2. Bifunctional Probes Reveal the Rules of Intracellular Ether Lipid Transport.Angewandte Chemie (International ed. in English) · 2025
    Article
  3. Synthesis of ether lipids: natural compounds and analogues.Beilstein journal of organic chemistry · 2023
    Review
  4. Article
  5. Total Synthesis of theOrganic letters · 2021
    Article
  6. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors at 1 institution in 1 country.

Lianyan L XuDepartment of Chemistry, Vanderbilt University, Nashville, TN 37235, USA. steven.d.townsend@vanderbilt.edu.
Lawrence J BergDepartment of Chemistry, Vanderbilt University, Nashville, TN 37235, USA. steven.d.townsend@vanderbilt.edu.ORCID 0000-0002-1462-0804
D Jamin KeithDepartment of Chemistry, Vanderbilt University, Nashville, TN 37235, USA. steven.d.townsend@vanderbilt.edu.ORCID 0000-0003-4611-927X
Steven D TownsendDepartment of Chemistry, Vanderbilt University, Nashville, TN 37235, USA. steven.d.townsend@vanderbilt.edu.ORCID 0000-0001-5362-7235
Vanderbilt University · US

Funding

Bioorganic Approaches Toward Novel Antimicrobial Agents and ChemotherapeuticsR35GM133602 · NIGMS · VANDERBILT UNIVERSITY · PI Steven D. Townsend · 2019 to 2026
$3.0M
NIGMS NIH HHS R35 GM133602
6 · The paper itself

Abstract

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.

Indexed as

AlcoholsAntiprotozoal AgentsIndicators and ReagentsModels, ChemicalOxidation-ReductionPhosphorylcholineAlcoholsAntiprotozoal AgentsIndicators and ReagentsmiltefosinePhosphorylcholine

Identifiers

PMID31912847
PMCPMC7047658
OpenAlexW2995236571

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.