dTDP–6–deoxy–4–keto–D–glucose (1), the common intermediate in the biosyntheses of the mainfold deoxysugars, was synthesized on a gram–scale by the combination of sucrose synthase and dTDP–D–glucose 4,6–dehydratase in a fed batch, starting the reaction with dTDP. This process allowed a dTDP conversion with a 100% rate. An easy and efficient three–step purification with anion–exchange chromatography and gel filtration gave 1.1 g of 1 in an overall yield of 73%. This work realizes a first step for an economic access to activated deoxysugars.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Die enzymatische Desoxygenierung von dTDP‐Glucose und zwei 3‐Desoxyanaloga [Gl. (a)] gelingt im präparativen Maßstab mit dTDP‐D‐Glucose‐4,6‐dehydratase. Zusammen mit einer selektiven HPLC‐Methode zur Trennung strukturell ähnlicher aktivierter Zucker lassen sich daraus Impulse für Struktur‐Funktions‐Untersuchungen an Desoxyzuckern und die weitere Aufklärung ihrer Biosynthesewege erwarten. R  OH, H, N3; dTDP = Thymidin‐5′‐diphosphat. magnified image

The application of sucrose synthase as a valuable biocatalyst for the synthesis of activated sugars and saccharides requires large amounts of enzyme. The purification of sucrose synthase starting from the 9 kg scale of rice (Oryza sativa) grains was achieved in five steps with 11.3% yield and 192-fold purification. The final sucrose synthase preparation was free of nucleotide di- and monophosphatases, but did contain 0.05% of both invertase and UDP-glucose-hydrolysing activity. It can be efficiently utilized for the synthesis of activated sugars. Its application for the synthesis of saccharides is possible taking into account that 15% UDP-glucose is hydrolysed within 15 h incubation time.