Carbohydrate chemistry

Symeres has gained considerable experience and  a proven track record in the intricate field of synthesizing  complex carbohydrates and their related derivatives. This specialized branch of organic synthesis can be challenging, primarily due to several complicating factors including  polarity, chemical complexity, the absence of a chromophore, and, in many cases, the  necessity for employing complex and bespoke  protection strategies for each of the targeted carbohydrates.

Our scientists at Symeres excel at tackling the numerous and multifaceted challenges that this unique field of organic chemistry presents, for example we have successfully navigated the synthesis of glucuronides of numerous active pharmaceutical ingredients (APIs) which are important tool compounds in the investigation of drug metabolism. Typically, there are several challenges associated with glucuronide synthesis; the chemist has to find the right conditions for coupling of the activated glucuronide moiety with the required substrate, and perform the subsequent mild removal of the protecting groups whilst retaining the glucuronide, and finally careful chromatography to obtain the final desired glucuronide product in high purity.For instance, we have synthesized SN-38 glucuronide, a metabolite of irinotecan, a topomerase inhibitor used for the treatment of various forms of cancer. Additionally, we have successfully produced 3-desmethylthiocolchicine-3-glucuronide, a metabolite of thiocolchicoside,  a muscle relaxant with anti-inflammatory and analgesic effects.

Diosmetin-3’-O-glucuronide and diosmetin-3’,7-di-O-glucuronide are metabolites of diosmin, a dietary supplement used to aid the treatment of hemorrhoids and venous diseases, both have been successfully synthesized at Symeres.

Benazepril acyl-β-D-glucuronide is a metabolite of benazepril, an ACE inhibitor used for the treatment of hypertension and congestive heart failure.

Benazepril acyl-β-D-glucuronide

All glucuronides depicted and more are available from our Chiralix catalog.

Another pillar of carbohydrate chemistry is centered around the preparation of disaccharides or tri-, tetra-, or higher oligosaccharides. This involves classical carbohydrate methodology and employing the appropriate protecting groups to join the building blocks together in the desired fashion to synthesize the required oligosaccharides.

Fondaparinux (Arixtra), a pentasaccharide anticoagulant with 25 chiral centers, is a classic example. Its chemical synthesis comprises over 60 reaction steps. Various impurities, in which one of the many chiral centers was inverted, were identified, characterized and synthesized at Symeres. Substituting one sugar moiety for another may look trivial but is far from it from a synthetic point of view, as the various sugars (glucose, galactose, idose, etc.) exhibit very different reactivities and therefore synthetic strategies cannot be readily transferred between different derivatives.


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