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

被引：2
|
作者：
Suchy, Mojmir [1 ,2 ]
Charlton, Thomas A. [1 ]
Ben, Robert N. [1 ]
Shuhendler, Adam J. [1 ,2 ]
机构：
[1] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON, Canada
[2] Univ Ottawa, Heart Inst, Ottawa, ON, Canada
来源：
CARBOHYDRATE RESEARCH | 2021年 / 507卷
基金：
加拿大自然科学与工程研究理事会;
关键词：
D-tagatose; D-fructose; Isotopic labelling; Rare carbohydrates; L-ARABINOSE ISOMERASE; D-GALACTOSE; DERIVATIVES;
D O I：
10.1016/j.carres.2021.108377
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
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页数：9
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