Evidence map›Paper›PMID 38590211›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2024

Exploring a De Novo Route to Bradyrhizose: Synthesis and Isomeric Equilibrium of Bradyrhizose Diastereomers

Vitor L S Cunha, George A O'Doherty, Todd L Lowary

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

3 authors.

Vitor L S CunhaDepartment of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.ORCID https://orcid.org/0000-0002-0607-7039
George A O'DohertyDepartment of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, 02115, USA.ORCID https://orcid.org/0000-0002-1699-2249
Todd L LowaryDepartment of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.ORCID https://orcid.org/0000-0002-8331-8211

Funding

De Novo Synthesis, and Functional and Structural Characterization of Novel Aminoglycoside Analogues to Bypass Resistance Mechanisms and Optimize SelectivityR01AI154860 · NIAID · BETH ISRAEL DEACONESS MEDICAL CENTER · PI KIRBY, JAMES E, O'DOHERTY, GEORGE A · 2020 to 2023
$3.1M
Apramycin scaffold exploration using novel glycochemistry and SAR studies to enhance activity against Acinetobacter baumannii and other multidrug-resistant Gram-negative pathogensR21AI142040 · NIAID · BETH ISRAEL DEACONESS MEDICAL CENTER · PI KIRBY, JAMES E, O'DOHERTY, GEORGE A · 2019 to 2020
$476k
Academia Sinica Intramural Funding from the Institute of Biological ChemistryCanadian Glycomics Network SD-1Directorate for Mathematical and Physical Sciences CHE-2102649National Institute of Allergy and Infectious Diseases AI142040National Institute of Allergy and Infectious Diseases AI154860Natural Sciences and Engineering Research Council of Canada RGPIN-2018-04365NIAID NIH HHS R01 AI154860NIAID NIH HHS R21 AI142040
6 · The paper itself

Abstract

A de novo asymmetric strategy for the synthesis of d-bradyrhizose diastereomers from an achiral ketoenolester precursor is described. Key transformations used in the stereodivergent approach include two Noyori asymmetric reductions, an Achmatowicz rearrangement, diastereoselective alkene oxidations, and the first example of a palladium(0)-catalyzed glycosylation of a vinylogous pyranone. The isomeric composition of the bicyclic reducing sugars obtained was analyzed and their behaviour was compared to the natural product, revealing key stereocentres that impact the overall distribution.

Indexed as

asymmetric synthesisbradyrhizosecarbohydratesde novo synthesistotal synthesis

Identifiers

PMID38590211
PMCPMC11168859

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Registered trials

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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.