General O-glycosylation of 2-furfuryl alcohol using beta-glucuronidase.
beta-Glucuronidase from bovine liver is able to catalyze transfer of several carbohydrates to furfuryl alcohol, an acid-sensitive diene, with transfer yields as high as 84%. Carbohydrates that were transferred in yields of 30% or higher include gluco-, galacto-, xylo-, and fucopyranose. Small variations in the configuration of the substrate hydroxyls lead to large variations in the catalytic behavior of the enzyme in terms of both the initial reaction velocities and the final ratios of transfer-to-hydrolysis. The high transfer yields and surprising nonspecificity towards carbohydrate suggest that the enzyme may be a versatile tool for the general O-glycosylation of dienic alcohols.
Martin
Brett D
BD
Center for BioMolecular Science and Engineering, Naval Research Laboratory, Washington, DC 20375-5348, USA. bdm@cbmse.nrl.navy.mil
Welsh
Eric R
ER
Mastrangelo
Jonathan C
JC
Aggarwal
Renu
R
D000818:Animals; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D002417:Cattle; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D005966:Glucuronidase / Q000096:biosynthesis / Q000737:chemistry*; D006031:Glycosylation; D008099:Liver / Q000201:enzymology; D008358:Mannose / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity
D002241:Carbohydrates; D005663:Furans; C434826:fucopyranosylamine; D005643:Fucose; C075822:glucopyranosylamine; C012986:furfuryl alcohol; D005966:Glucuronidase; D005944:Glucosamine; D008358:Mannose; D005690:Galactose