Evidence map›Paper›PMID 36573850›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Influence of Side Chain Conformation on the Activity of Glycosidase Inhibitors.

Po-Sen Tseng, Chennaiah Ande, Kelley W Moremen, David Crich

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.

0numbers the graph read from it
0cells of the map it votes in
38citing 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

38 citing papers in PubMed.

  1. Trial
  2. Article
  3. Unnatural C6-Substituted d-Galactosides as Attenuated Substrates of Glycosyl Hydrolases.Chembiochem : a European journal of chemical biology · 2026
    Article
  4. Article
  5. Review
  6. Article
  7. Pharmaceuticals (Basel, Switzerland) · 2024
    Article
  8. Review
  9. Review
  10. Pharmaceuticals (Basel, Switzerland) · 2024
    Article
  11. Article
  12. Article
  13. Hypoglycemic Effects and Quality Marker Screening ofMolecules (Basel, Switzerland) · 2024
    Article
  14. Article
  15. Review
  16. Review
  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

4 authors.

Po-Sen TsengDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, GA-30602, USA.ORCID 0000-0003-2860-5725
Chennaiah AndeDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, GA-30602, USA.ORCID 0000-0002-7599-894X
Kelley W MoremenComplex Carbohydrate Research Center, University of Georgia, Athens, GA-30602, USA.ORCID 0000-0003-1768-582X
David CrichDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, GA-30602, USA.ORCID 0000-0003-2400-0083

Funding

Resource for Biocomputing Visualization and InformaticsP41GM103311 · NIGMS · UNIVERSITY OF CALIFORNIA, SAN FRANCISCO · PI FERRIN, THOMAS E · 2012 to 2017
$8.2M
Methods and Mechanisms in Carbohydrate ChemistryR01GM062160 · NIGMS · WAYNE STATE UNIVERSITY · PI CRICH, DAVID · 2001 to 2024
$7.1M
NIGMS NIH HHS P41 GM103311NIGMS NIH HHS R01 GM062160
6 · The paper itself

Abstract

Substrate side chain conformation impacts reactivity during glycosylation and glycoside hydrolysis and is restricted by many glycosidases and glycosyltransferases during catalysis. We show that the side chains of gluco and manno iminosugars can be restricted to predominant conformations by strategic installation of a methyl group. Glycosidase inhibition studies reveal that iminosugars with the gauche,gauche side chain conformations are 6- to 10-fold more potent than isosteric compounds with the gauche,trans conformation; a manno-configured iminosugar with the gauche,gauche conformation is a 27-fold better inhibitor than 1-deoxymannojirimycin. The results are discussed in terms of the energetic benefits of preorganization, particularly when in synergy with favorable hydrophobic interactions. The demonstration that inhibitor side chain preorganization can favorably impact glycosidase inhibition paves the way for improved inhibitor design through conformational preorganization.

Indexed as

1-DeoxynojirimycinGlycoside HydrolasesEnzyme InhibitorsGlycosidesMolecular Conformation1-DeoxynojirimycinEnzyme InhibitorsGlycoside HydrolasesGlycosidesGlycosidaseIminosugarInhibitorMethyl GroupSide Chain Conformation

Identifiers

PMID36573850
PMCPMC9908843

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.