Book of abstracts version 5

Synthesis thiodigalactoside building blocks, towards anticancer
or anti-inflammatory drugs.
Author
Thijs Verdaasdonk
Academy of Technology for Health and Environment
Avans Hogeschool, Breda
Universiteit Utrecht
Nishant Sewgobind
Abstract
Between all the proteins galectin is defined by its affinity for β-galactoside. Galectins function intracellularly,
extracellularly and they are involved in a range of biological processes. Many of these processes are beneficial f or a
person’s health but these proteins also play a role in some pathological processes. Despite all this the exact biological rol e
of galectins remains questionable. For further research an inhibitor is needed to be able to conduct experiments with
these galectins. [1] The inhibitor is a thiodigalactoside molecule wherefor the basic building block a β -galactoside namely
3-O-acetyl-1,2;5,6-di-O-isopropylidene-α-D-gulofuranose(4) will be synthesized from 1,2,5,6 -diacetone-α-Dglucofuranose(1).
The complete synthesis will be displayed in the table of content(figure 1) it consists of 3 steps with an
expected conversion rate of 70%. The first step is a oxidation with pyridinium dichromate, this product will be acetylated
with DABCO and acetic anhydride and the final step is a hydrogenation using palladium on carbon. All products are
purified by column chromatography and analysed with TLC, H -NMR and FTIR.[2]
Keywords: Thiodigalactoside, galectin, inhibitor, β-galactoside and Diacetone-D-glucose.
Table of content
Figure 1: reaction scheme full synthesis from 1,2,5,6-diacetone-α-D-glucofuranose(1) to 3-O-acetyl-1,2;5,6-di-Oisopropylidene-α-D-gulofuranose(4).
[1] S. Karger, „The Role of Galectin-3 as a Marker of Cancer and inflammation in a stage IV Ovarian Cancer Patient with
Underlying Pro-Inflammatory Comorbidities,” Case reports in oncology, nr. 6, pp. 343 -349, 2013.
[2] H. van Hattum en e. all., „Tuning the Preference of Thiodigalactoside- and Lactosamine-Based,” Journal of Medicinal
Chemistry, nr. 56, pp. 1350-1354, 2013.
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