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Enzymatic Synthesis of ß-L-Fucose-1-phosphate and GDP-fucose

✍ Scribed by Stiller, Regine ;Thiem, Joachim

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
562 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Fucose is an important component of complex heterooligosaccharides. Here we describe the preparative enzymatic synthesis of ß‐L‐fucose‐1‐phosphate as well as its enzymatic conversion into GDP‐fucose. Fucose (1) was converted into ß‐L‐fucose‐1‐phosphate (2) with fucose kinase (EC 2.7.1.52) obtained from porcine submaxillary glands by consumption of ATP. Syntheses carried out with the enzymes enclosed in a dialysis bag gave 19% yield of ß‐L‐fucose‐1‐phosphate. Application of the enzymes in a batch procedure using an ultrafiltration cell gave 40% yield of the fucose‐1‐phosphate. The yield could be increased to 80% if the inhibitor ADP was removed by cofactor regeneration with phosphoenolpyruvate. ß‐L‐Fucose‐1‐phosphate was isolated as various salts and analyzed by NMR spectroscopy. In a second enzymatic reaction ß‐L‐fucose‐1‐phosphate was converted into GDP‐fucose (3) by the action of GDP‐fucose pyrophosphorylase (EC 2.7.7.30) obtained from porcine submaxillary glands. In a 50‐μmolar scale reaction, yields around 20% were obtained.

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