Evidence map›Paper›PMID 32856761›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.

Thomas Hansen, Tim P Ofman, Joey G C Vlaming, Ivan A Gagarinov, Jessey van Beek, Tessa A Goté, Jacoba M Tichem, Gijs Ruijgrok, Herman S Overkleeft, Dmitri V Filippov and 2 more

Open access · hybridAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. 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
1.6field-weighted citation impact, top 18% 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, 23 citations in OpenAlex.

  1. Synthesis ofScience advances · 2025
    Article
  2. Article
  3. Article
  4. Article
  5. Competing C-4 and C-5-Acyl Stabilization of Uronic Acid Glycosyl Cations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  6. Review
  7. 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

12 authors at 1 institution in 1 country.

Thomas HansenLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0002-6291-1569
Tim P OfmanLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0002-1687-2191
Joey G C VlamingLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0002-6493-5783
Ivan A GagarinovLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0003-1742-3870
Jessey van BeekLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Tessa A GotéLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Jacoba M TichemLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Gijs RuijgrokLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Herman S OverkleeftLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Dmitri V FilippovLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0002-6978-7425
Gijsbert A van der MarelLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0001-8917-3458
Jeroen D C CodéeLeiden University, Leiden Institute of Chemistry, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.ORCID 0000-0003-3531-2138
Leiden University · NL

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions in which they partake. We here report a strategy to map the reactivity of carbohydrate building blocks and apply it to understand the reactivity of the bacterial sugar, caryophyllose, a rare C12-monosaccharide, containing a characteristic tetrasubstituted stereocenter. We mapped reactivity-stereoselectivity relationships for caryophyllose donor and acceptor glycosides by a systematic series of glycosylations in combination with the detection and characterization of different reactive intermediates using experimental and computational techniques. The insights garnered from these studies enabled the rational design of building blocks with the required properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.

Indexed as

Bacterial ProteinsDensity Functional TheoryGlycosylationLipopolysaccharidesMycobacterium marinumStereoisomerismBacterial Proteinslipid-linked oligosaccharidesLipopolysaccharidesdensity functional calculationsglycosylationglycosyl cationreactivitystereoselectivity

Identifiers

PMID32856761
PMCPMC7821131
OpenAlexW3081743034

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.