Skip to main content

Research Repository

Advanced Search

Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose.

Porter, Jack; Lima, Marcelo A.; Pongener, Imlirenla; Miller, Gavin

Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. Thumbnail


Authors

Imlirenla Pongener



Abstract

Sulfur containing glycosides offer an exciting prospect for inclusion within noncanonical glycan sequences, particularly as enabling probes for chemical glycobiology and for carbohydrate-based therapeutic development. In this context, we required access to 4-thio-d-glucopyranose and sought its chemical synthesis. Unable to isolate this material in homogenous form, we observed instead a thermodynamic preference for interconversion of the pyranose to 4-thio-d-glucofuranose. Accordingly, we present an improved method to access both bis(4-thio-d-glucopyranoside)-4,4'-disulfide and 4-thio-d-glucofuranose from a single precursor, demonstrating that the latter compound can be accessed from the former using a dithiothreitol controlled reduction of the disulfide. The dithiothreitol-mediated interconversion between pyranose (monomer and disulfide) and furanose forms for this thiosugar is monitored by 1H NMR spectroscopy over a 24-h period. Access to these materials will support accessing sulfur-containing mimetics of glucose and derivatives therefrom, such as sugar nucleotides.

Citation

Porter, J., Lima, M. A., Pongener, I., & Miller, G. (2023). Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. Carbohydrate Research, 524, Article 108759. https://doi.org/10.1016/j.carres.2023.108759

Journal Article Type Article
Acceptance Date Jan 23, 2023
Online Publication Date Jan 24, 2023
Publication Date Feb 1, 2023
Publicly Available Date May 30, 2023
Journal Carbohydrate Research
Print ISSN 0008-6215
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 524
Article Number 108759
DOI https://doi.org/10.1016/j.carres.2023.108759
Publisher URL https://www.sciencedirect.com/science/article/pii/S0008621523000216?via%3Dihub
Additional Information
© 2023 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

Files




You might also like



Downloadable Citations