Evidence map›Paper›PMID 20439750›Full record

ArticleProceedings of the National Academy of Sciences of the United States of America2010

Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

Peter A Jordan, Katherine J Kayser-Bricker, Scott J Miller

Open access · greenAbstract read
In one paragraph

Article in Proceedings of the National Academy of Sciences of the United States of America, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.

0numbers the graph read from it
0cells of the map it votes in
18citing papers in PubMed
3.9field-weighted citation impact, top 6% 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

18 citing papers in PubMed, 77 citations in OpenAlex.

  1. Article
  2. Review
  3. Article
  4. Article
  5. Article
  6. Article
  7. Review
  8. Catalytic ChemoselectiveACS central science · 2020
    Article
  9. Article
  10. Article
  11. Article
  12. Review
  13. Article
  14. Site-selective bromination of vancomycin.Journal of the American Chemical Society · 2012
    Article
  15. Article
  16. Article
  17. Scaffolding catalysts: highly enantioselective desymmetrization reactions.Angewandte Chemie (International ed. in English) · 2011
    Article
  18. Organocatalysis.Proceedings of the National Academy of Sciences of the United States of America · 2010
    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

3 authors at 1 institution in 1 country.

Peter A JordanDepartment of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-4900, USA.
Katherine J Kayser-Bricker
Scott J Miller
Yale University · US

Funding

Site-Selective Catalysis for Organic SynthesisR37GM068649 · NIGMS · YALE UNIVERSITY · PI MILLER, SCOTT J · 2011 to 2018
$2.7M
Site-Selective Catalysts for Organic SynthesisR01GM068649 · NIGMS · YALE UNIVERSITY · PI MILLER, SCOTT J · 2003 to 2010
$2.3M
NIGMS NIH HHS GM-068649NIGMS NIH HHS R01 GM068649NIGMS NIH HHS R37 GM068649
6 · The paper itself

Abstract

Despite the ubiquitous use of phosphoramidite chemistry in the synthesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for phosphate ester synthesis. We have discovered that a tetrazole-functionalized peptide, in the presence of 10-Å molecular sieves, functions as an enantioselective catalyst for phosphite transfer. This chemistry in turn has been used as the key step in a streamlined synthesis of myo-inositol-6-phosphate. Mechanistic insights implicate phosphate as a directing group for a highly selective kinetic resolution of a protected inositol monophosphate. This work represents a distinct and efficient method for the selective catalytic phosphorylation of natural products.

Indexed as

BiocatalysisIndicators and ReagentsInositol PhosphatesOrganophosphorus CompoundsPhosphorylationStereoisomerismIndicators and ReagentsInositol PhosphatesOrganophosphorus Compoundsphosphoramidite

Identifiers

PMID20439750
PMCPMC2996443
OpenAlexW2143380036

What OpenQuestion holds

Textmetadata
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.