Evidence map›Paper›PMID 31083938›Full record

ArticleThe Journal of organic chemistry2019

9-Azido-9-deoxy-2,3-difluorosialic Acid as a Subnanomolar Inhibitor against Bacterial Sialidases.

Wanqing Li, Abhishek Santra, Hai Yu, Teri J Slack, Musleh M Muthana, Dashuang Shi, Yang Liu, Xi Chen

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing papers in PubMed
0.5field-weighted citation impact, top 36% 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

7 citing papers in PubMed, 15 citations in OpenAlex.

  1. Article
  2. Proceedings of the National Academy of Sciences of the United States of America · 2024
    Article
  3. Article
  4. Sialidase Inhibitors with Different Mechanisms.Journal of medicinal chemistry · 2022
    Review
  5. Review
  6. Review
  7. 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

8 authors at 2 institutions in 1 country.

Wanqing LiDepartment of Chemistry , University of California-Davis , One Shields Avenue , Davis , California 95616 , United States.
Abhishek SantraDepartment of Chemistry , University of California-Davis , One Shields Avenue , Davis , California 95616 , United States.ORCID 0000-0002-5620-629X
Hai YuDepartment of Chemistry , University of California-Davis , One Shields Avenue , Davis , California 95616 , United States.ORCID 0000-0002-4378-0532
Teri J SlackDepartment of Chemistry , University of California-Davis , One Shields Avenue , Davis , California 95616 , United States.
Musleh M Muthana
Dashuang Shi
Yang Liu
Xi ChenDepartment of Chemistry , University of California-Davis , One Shields Avenue , Davis , California 95616 , United States.ORCID 0000-0002-3160-614X
University of California, Davis · USChildren's National · US

Funding

Supplement: Exploring the biology of O-acetyl sialic acids using stable synthetic mimicsR01AI130684 · NIAID · UNIVERSITY OF CALIFORNIA AT DAVIS · PI CHEN, XI, VARKI, AJIT P · 2017 to 2020
$2.3M
Targeting endogenous sialidases for treatment of endotoxic shockR43AI108115 · NIAID · ONCOIMMUNE, INC. · PI QIU, PING · 2014 to 2015
$395k
NIAID NIH HHS R01 AI130684NIAID NIH HHS R43 AI108115
6 · The paper itself

Abstract

A library of 2(a),3(a/e)-difluorosialic acids and their C-5 and/or C-9 derivatives were chemoenzymatically synthesized. Pasteurella multocida sialic acid aldolase (PmAldolase), but not its Escherichia coli homologue (EcAldolase), was found to catalyze the formation of C5-azido analogue of 3-fluoro(a)-sialic acid. In comparison, both PmAldolase and EcAldolase could catalyze the synthesis of 3-fluoro(a/e)-sialic acids and their C-9 analogues although PmAldolase was generally more efficient. The chemoenzymatically synthesized 3-fluoro(a/e)-sialic acid analogues were purified and chemically derivatized to form the desired difluorosialic acids and derivatives. Inhibition studies against several bacterial sialidases and a recombinant human cytosolic sialidase hNEU2 indicated that sialidase inhibition was affected by the C-3 fluorine stereochemistry and derivatization at C-5 and/or C-9 of the inhibitor. Opposite to that observed for influenza A virus sialidases and hNEU2, compounds with axial fluorine at C-3 were better inhibitors (up to 100-fold) against bacterial sialidases compared to their 3F-equatorial counterparts. While C-5-modified compounds were less-efficient antibacterial sialidase inhibitors, 9-N

Indexed as

Carbohydrate ConformationEnzyme InhibitorsNeuraminidasePasteurella multocidaSialic AcidsEnzyme InhibitorsNeuraminidaseSialic Acids

Identifiers

PMID31083938
PMCPMC6660241
OpenAlexW2945750250

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.