Evidence map›Paper›PMID 32755675›Full record

ArticleCarbohydrate research2020

Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.

Riku Ogasahara, Shuay Abdullayev, Vikram A Sarpe, Appi Reddy Mandhapati, David Crich

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

Article in Carbohydrate research, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.4field-weighted citation impact, top 44% 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

2 citing papers in PubMed, 8 citations in OpenAlex.

  1. Comparison of glycosyl donors: a supramer approach.Beilstein journal of organic chemistry · 2024
    Article
  2. Synthesis of 3-Deoxy-d-The Journal of organic chemistry · 2020
    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 at 3 institutions in 3 countries.

Riku OgasaharaDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA; Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa, 223-8522, Japan.
Shuay AbdullayevDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA; Department of Chemistry, Université Claude Bernard Lyon 1, Domaine Scientifique de la Doua, boulevard du 11 Novembre 1918, 69622, Villeurbanne Cedex, France.
Vikram A SarpeDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, United States; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, United States.
Appi Reddy MandhapatiDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA.
David CrichDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA; Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, United States; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, United States; Department of Chemistry, University of Georgia, 140 Cedar Street, Athens, GA, 30602, United States. Electronic address: david.crich@uga.edu.
University of Georgia · USWayne State University · USUniversité Claude Bernard Lyon 1 · FR

Funding

Methods and Mechanisms in Carbohydrate ChemistryR01GM062160 · NIGMS · WAYNE STATE UNIVERSITY · PI CRICH, DAVID · 2001 to 2024
$7.1M
NIGMS NIH HHS R01 GM062160
6 · The paper itself

Abstract

The adamantanyl thioglycosides of 5-isothiocyano and 5-azido 5-desamino-4,7,8,9-tetra-O-acetylneuraminic acid methyl ester were converted into the corresponding dibutyl phosphates, which proved to be excellent α-selective donors for O-sialidation with a range of typical acceptors, and good donors for reaction with allyltributylstannane, albeit without significant anomeric selectivity. In the KDN series the dibuylphosphate derived from a donor carrying a 4,5-cyclic carbonate protecting group afforded the corresponding C-glycoside with excellent α-selectivity on activation in the presence of allyltributylstannane, whereas the corresponding donor carrying acetate esters at the 4- and 5-positions was unselective. Overall, it is revealed that while the strongly electron-withdrawing isothiocyanato and azido groups are sufficient to promote highly α-selective O-sialidation, they are inadequate when faced with less reactive nucleophiles when mixtures of anomers are obtained.

Indexed as

CarbonGlycosylationOxygenPhosphatesStereoisomerismThioglycosidesCarbonOxygenPhosphatesThioglycosidesC-GlycosidesGlycosyl phosphatesKDN C-GlycosideNeuraminic acidSialidation

Identifiers

PMID32755675
PMCPMC7484008
OpenAlexW3045736201

What OpenQuestion holds

Textmetadata
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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.