Evidence map›Paper›PMID 34584948›Full record

ReviewACS central science2021

Nature Chose Phosphates and Chemists Should Too: How Emerging P(V) Methods Can Augment Existing Strategies.

Kyle W Knouse, Dillon T Flood, Julien C Vantourout, Michael A Schmidt, Ivar M Mcdonald, Martin D Eastgate, Phil S Baran

Open access · diamondAbstract readReview
In one paragraph

Review in ACS central science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.

0numbers the graph read from it
0cells of the map it votes in
29citing papers in PubMed
5.9field-weighted citation impact, top 3% 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

29 citing papers in PubMed, 97 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Conception and Synthesis of Sequence-Coded Morpholinos.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  6. Controlling Glycan Folding with Ionic Functional Groups.Journal of the American Chemical Society · 2025
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Chemical strategies for antisense antibiotics.Chemical Society reviews · 2024
    Review
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. 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

7 authors at 2 institutions in 1 country.

Kyle W KnouseElsie Biotechnologies, 4955 Directors Place, San Diego, California 92121, United States.ORCID https://orcid.org/0000-0001-9688-0513
Dillon T FloodElsie Biotechnologies, 4955 Directors Place, San Diego, California 92121, United States.ORCID https://orcid.org/0000-0002-6600-0287
Julien C VantouroutDepartment of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID https://orcid.org/0000-0002-0602-069X
Michael A SchmidtChemical and Synthetic Development, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.ORCID https://orcid.org/0000-0002-4880-2083
Ivar M McdonaldSmall Molecule Drug Discovery, Bristol Myers Squibb, 100 Binney Street, Cambridge, Massachusetts 02142, United States.
Martin D EastgateChemical and Synthetic Development, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.ORCID https://orcid.org/0000-0002-6487-3121
Phil S BaranElsie Biotechnologies, 4955 Directors Place, San Diego, California 92121, United States.ORCID https://orcid.org/0000-0001-9193-9053
Scripps Institution of Oceanography · USBristol-Myers Squibb (United States) · US

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
NRSA Training CoreTL1TR002551 · NCATS · SCRIPPS RESEARCH INSTITUTE, THE · PI TEYTON, LUC · 2018 to 2022
$1.2M
NCATS NIH HHS TL1 TR002551NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

Phosphate linkages govern life as we know it. Their unique properties provide the foundation for many natural systems from cell biology and biosynthesis to the backbone of nucleic acids. Phosphates are ideal natural moieties; existing as ionized species in a stable P(V)-oxidation state, they are endowed with high stability but exhibit enzymatically unlockable potential. Despite intense interest in phosphorus catalysis and condensation chemistry, organic chemistry has not fully embraced the potential of P(V) reagents. To be sure, within the world of chemical oligonucleotide synthesis, modern approaches utilize P(III) reagent systems to create phosphate linkages and their analogs. In this Outlook, we present recent studies from our laboratories suggesting that numerous exciting opportunities for P(V) chemistry exist at the nexus of organic synthesis and biochemistry. Applications to the synthesis of stereopure antisense oligonucleotides, cyclic dinucleotides, methylphosphonates, and phosphines are reviewed as well as chemoselective modification to peptides, proteins, and nucleic acids. Finally, an outlook into what may be possible in the future with P(V) chemistry is previewed, suggesting these examples represent just the tip of the iceberg.

Identifiers

PMID34584948
PMCPMC8461637
OpenAlexW3201372641

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
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.