Evidence map›Paper›PMID 29713033›Full record

ArticleNature chemistry2018

Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent.

Tyler J Wadzinski, Angela Steinauer, Liana Hie, Guillaume Pelletier, Alanna Schepartz, Scott J Miller

Open access · greenAbstract read
In one paragraph

Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.

0numbers the graph read from it
0cells of the map it votes in
41citing papers in PubMed
6.4field-weighted citation impact, top 2% 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

41 citing papers in PubMed, 141 citations in OpenAlex.

  1. Article
  2. StereoselectiveJACS Au · 2026
    Article
  3. Article
  4. Article
  5. Synthesis and Structural Confirmation of Secalosides A and B.Journal of the American Chemical Society · 2026
    Article
  6. Article
  7. Protective Effects ofAntioxidants (Basel, Switzerland) · 2025
    Article
  8. Article
  9. Article
  10. Cooperative Catalysis in StereoselectiveJournal of the American Chemical Society · 2024
    Article
  11. Article
  12. Unconventional posttranslational modification in innate immunity.Cellular and molecular life sciences : CMLS · 2024
    Review
  13. Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Review
  19. Chemistry and Bioactivity ofMolecules (Basel, Switzerland) · 2022
    Article
  20. Review
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

6 authors at 1 institution in 1 country.

Tyler J WadzinskiDepartment of Chemistry, Yale University, New Haven, CT, USA.
Angela SteinauerDepartment of Chemistry, Yale University, New Haven, CT, USA.
Liana HieDepartment of Chemistry, Yale University, New Haven, CT, USA.
Guillaume PelletierDepartment of Chemistry, Yale University, New Haven, CT, USA.ORCID http://orcid.org/0000-0002-3485-5416
Alanna SchepartzDepartment of Chemistry, Yale University, New Haven, CT, USA. alanna.schepartz@yale.edu.ORCID http://orcid.org/0000-0003-2127-3932
Scott J MillerDepartment of Chemistry, Yale University, New Haven, CT, USA. scott.miller@yale.edu.ORCID http://orcid.org/0000-0001-7817-1318
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
Development of Site-Selective Glycosylation of Unprotected SugarsF32GM122204 · NIGMS · YALE UNIVERSITY · PI HIE, LIANA · 2017 to 2017
$56k
NIGMS NIH HHS F32 GM122204NIGMS NIH HHS R01 GM068649NIGMS NIH HHS R37 GM068649
6 · The paper itself

Abstract

Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small molecules, unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)

Indexed as

Amino AcidsCalcium HydroxideCarbon-13 Magnetic Resonance SpectroscopyChromatography, High Pressure LiquidGlycosylationPeptidesPhenolsProton Magnetic Resonance SpectroscopySmall Molecule LibrariesSolventsTandem Mass SpectrometryWaterAmino AcidsCalcium HydroxidePeptidesPhenolsSmall Molecule LibrariesSolventsWater

Identifiers

PMID29713033
PMCPMC5964040
OpenAlexW2800748443

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.