Development of a technological procedure for 6-deoxy saccharides

Fig. 1: 6-deoxy-glucose.

6-dexy-glucose is a high added value chemical specialty used in pharmaceutical and food industry. Its synthesis generally consists of multiple reaction steps, leading to low product yields and long production times. Due to the application of the compound in food stuffs and drugs, excellent purity of the final product is required, resulting in the need for complex separation processes.

6-deO-glc is a biologically active compound, its main effect being the inhibition of hexokinase. This effect led to its use as an antimetabolite. It is also present in various types of drugs (antihypertensives, analgesics, antineoplastics) and drug formulations (sustained release formulations, cryoprotectants). In the food industry, 6-deO-glc is used as a dye and a flavoring agent.

The main problem in the synthesis is the selectivity of reactions - due to a large number of functional groups in the glucose molecule, it is necessary to develop highly selective processes affecting only the C6 reaction center. Any reactions in other positions are the sources of contamination in the final product. Standard procedure for the synthesis of 6-deoxy glucose is multiple-step synthesis combined with sophisticated separation methods, such as column chromatography. These methods significantly increase the price of the industrial production of 6-deO-glc.

A new synthetic approach, developed at the Department of Organic Technology, ICT Prague, allows the synthesis of 6-deoxy-glucose in four simple reaction steps. Synthesis affords up to 41% yield of the substance with 99.5% purity. No costly separation techniques are necessary, synthesis does not require pressure apparatus and impurities in the final product do not contain toxic heavy metals. The whole synthetic process takes four days, including the final crystallization step.

Due to the simplicity of synthesis and separation of the developed procedure, the estimated price of the process is significantly lower than that of other industrially used methods.

The subject of current research is the application of the procedure for a wide range of carbohydrates, including other hexoses (carbohydrates containing six carbon atoms) and also possibly pentoses and heptoses. These developments should increase the applicability of the process for the production of valuable carbohydrate derivatives.