Synthesis of natural/13C-enriched d-tagatose from natural/13C-enriched d-fructose

Mojmír Suchý; Thomas A Charlton; Robert N Ben; Adam J Shuhendler

doi:10.1016/j.carres.2021.108377

Synthesis of natural/¹³C-enriched d-tagatose from natural/¹³C-enriched d-fructose

Carbohydr Res. 2021 Sep:507:108377. doi: 10.1016/j.carres.2021.108377. Epub 2021 Jun 16.

Authors

Mojmír Suchý¹, Thomas A Charlton², Robert N Ben², Adam J Shuhendler³

Affiliations

¹ Department of Chemistry & Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada; University of Ottawa Heart Institute, Ottawa, Ontario, Canada.
² Department of Chemistry & Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada.
³ Department of Chemistry & Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada; University of Ottawa Heart Institute, Ottawa, Ontario, Canada. Electronic address: ashuhend@uottawa.ca.

PMID: 34303197
DOI: 10.1016/j.carres.2021.108377

Abstract

A concise, easily scalable synthesis of a rare ketohexose, d-tagatose, was developed, that is compatible with the preparation of d-[UL-¹³C₆]tagatose. Epimerization of the widely available and inexpensive ketohexose d-fructose at the C-4 position via an oxidation/reduction (Dess-Martin periodinane/NaBH₄) was a key step in the synthesis. Overall, fully protected natural d-tagatose (3.21 g) was prepared from d-fructose (9 g) on a 50 mmol scale in 23% overall yield, after five steps and two chromatographic purifications. d-[UL-¹³C₆]Tagatose (92 mg) was prepared from d-[UL-¹³C₆]fructose (465 mg, 2.5 mmol) in 16% overall yield after six steps and four chromatographic purifications.

Keywords: Isotopic labelling; Rare carbohydrates; d-[UL-13C6]fructose; d-[UL-13C6]tagatose; d-fructose; d-tagatose.

MeSH terms

Carbon Isotopes
Chemistry Techniques, Synthetic
Fructose* / chemical synthesis
Fructose* / chemistry
Hexoses* / chemical synthesis
Hexoses* / chemistry
Oxidation-Reduction

Substances

Hexoses
tagatose
Fructose
Carbon-13
Carbon Isotopes