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Synthesis of Uridine 5′-(α-D-Fucopyranosyl Diphosphate) and (Digitoxigenin-3β-yl)-β-D-Fucopyranoside and Enzymatic β-D-Fucosylation of Cardenolide Aglycones in Digitalis lanata1

✍ Scribed by T. Faust; C. Theurer; K. Eger; W. Kreis

Book ID: 102966038
Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 577 KB
Volume: 22
Category: Article
ISSN: 0045-2068
DOI: 10.1006/bioo.1994.1012

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✦ Synopsis

The phosphorylation of 2,3,4-tri-O-acetyl- (\alpha)-D-fucopyranose with (\sigma)-phenylene phosphochloridate yielded (\alpha \cdot) D-fucopyranosyl phosphate which was used for condensation with uridine 5 '-monophosphomorpholidate to give uridine (5^{\prime})-( (\alpha)-D-fucopyranosyl diphosphate) (UDP- (\alpha)-D-fucose). A crude enzyme preparation from young leaves of Digitalis lanata EHRH has been shown to catalyze the transfer of (\mathrm{D})-fucose from synthetic UDP- (\alpha)-D-fucose to cardenolide aglycones, such as digitoxigenin. The reaction product was identified and characterized by chemical synthesis, HPLC, and spectral methods as the (3 \beta-O-\beta)-D-fucopyranoside of digitoxigenin (digiproside). 1994 Academic Press, Inc.

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