Evidence map›Paper›PMID 29227649›Full record

ArticleThe Journal of organic chemistry2018

Regenerative Glycosylation.

Yashapal Singh, Tinghua Wang, Scott A Geringer, Keith J Stine, Alexei V Demchenko

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.

0numbers the graph read from it
0cells of the map it votes in
22citing papers in PubMed
–field-weighted citation impact
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

22 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Review
  6. HPLC-Based Automated Synthesis of Glycans in Solution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Diastereoselective spACS catalysis · 2020
    Article
  12. Defining the Scope of the Acid-Catalyzed Glycosidation of Glycosyl Bromides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020
    Article
  13. Article
  14. Article
  15. Bromine-Promoted Glycosidation of Conformationally Superarmed Thioglycosides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019
    Article
  16. Recent Developments in Stereoselective Chemical Glycosylation.Asian journal of organic chemistry · 2019
    Article
  17. Phenanthroline-Catalyzed Stereoretentive Glycosylations.Angewandte Chemie (International ed. in English) · 2019
    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

5 authors.

Yashapal SinghDepartment of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Tinghua WangDepartment of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Scott A GeringerDepartment of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Keith J StineDepartment of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Alexei V DemchenkoDepartment of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.ORCID 0000-0003-3515-212X

Funding

Automation of the chemical synthesis of human milk oligosaccharidesR01GM111835 · NIGMS · SAINT LOUIS UNIVERSITY · PI DEMCHENKO, ALEXEI V · 2014 to 2023
$2.5M
Refinement and implementation of the automated oligosaccharide synthesizerU01GM120673 · NIGMS · UNIVERSITY OF MISSOURI-ST. LOUIS · PI DE MEO, CRISTINA, DEMCHENKO, ALEXEI V · 2016 to 2019
$2.2M
NIGMS NIH HHS R01 GM111835NIGMS NIH HHS U01 GM120673
6 · The paper itself

Abstract

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

Indexed as

Carbohydrate ConformationGlycosylationOligosaccharidesSugarsOligosaccharidesSugars

Identifiers

PMID29227649
PMCPMC5971087

What OpenQuestion holds

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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.