Unusual C-C bond cleavage of an α-trifloxy Sialic acid hemiacetal under Lattrell-Dax conditions.

Santanu Jana, David Crich

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Article in Carbohydrate research, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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0citing papers in PubMed

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1 · What the graph read from it

What it found

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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

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3 · Its place in the literature

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0 citing papers in PubMed, 0 citations in OpenAlex.

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5 · Who and what money

Authors and funding

2 authors at 1 institution in 1 country.

Santanu JanaDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, USA; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, USA.

David CrichDepartment of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, GA, 30602, USA; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA, 30602, USA; Department of Chemistry, University of Georgia, 140 Cedar Street, Athens, GA, 30602, USA. Electronic address: David.crich@uga.edu.

University of Georgia · US

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

We describe the novel oxidative fragmentation of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-trifluoromethanesulfonyl-β-D-erythro-L-gluco-2-nonulopyranos)onate 2 on stirring with sodium nitrite in DMF to give the novel 3-acetamido-2,5,6,7-tetra-O-acetyl-d-glycero-d-galacto-heptono-1,4-lactone 3 in excellent yield. Stirring of the same triflate with sodium carbonate on the other hand affords the novel methyl (5-acetamido-7,8,9-tri-O-acetyl-3,6-anhydro-5-deoxy-d-manno-3-ene-2-nonulos)onate 19 also in excellent yield. Reduction of the heptono lactone with sodium borohydride followed by acetylation gives a peracetylated aminodeoxyheptitol 6 that adopts the zig zag conformation of its carbon backbone.

Indexed as

N-Acetylneuraminic AcidCarbohydrate ConformationCarbohydrate SequenceN-Acetylneuraminic AcidConformational analysisFuranolactoneLattrell-Dax reactionOxidative cleavageSialic acid

Identifiers

PMID34959032

DOI10.1016/j.carres.2021.108494

PMCPMC8792320

OpenAlexW4200021480

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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.