Synthesis of natural/13C-enriched d-tagatose from natural/13C-enriched d-fructose. (September 2021)

• Record Type: Journal Article
• Authors: Suchý, Mojmír; Charlton, Thomas A.; Ben, Robert N.; Shuhendler, Adam J.
• Is Part Of: Carbohydrate research. Volume 507(2021)
• Publication Date: 2021-09
• Subjects: d-tagatose -- d-fructose -- d-[UL-13C6]tagatose -- d-[UL-13C6]fructose -- Isotopic labelling -- Rare carbohydrates; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2021.108377
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A concise, easily scalable synthesis of a rare ketohexose, d -tagatose, was developed, that is compatible with the preparation of d -[UL- 13 C6 ]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- 13 C6 ]Tagatose (92 mg) was prepared from d -[UL- 13 C6 ]fructose (465 mg, 2.5 mmol) in 16% overall yield after six steps and four chromatographic purifications. Graphical abstract: Image 1