Combined preparative enzymatic synthesis of dTDP-6-deoxy-4-keto-D-glucose from dTDP and sucrose.
dTDP-6-deoxy-4-keto-D-glucose (1), the common intermediate in the biosyntheses of the manifold 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.
Stein
A
A
Institute of Enzyme Technology, Heinrich-Heine-University Düsseldorf in the research centre Jülich, Germany.
Kula
M R
MR
Elling
L
L
D001709:Biotechnology / Q000379:methods; D004926:Escherichia coli / Q000235:genetics; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000378:metabolism; D005964:Glucosyltransferases / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D006836:Hydro-Lyases / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D011994:Recombinant Proteins / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism; D012486:Salmonella typhimurium / Q000201:enzymology; D013395:Sucrose / Q000737:chemistry / Q000378:metabolism*; D013942:Thymine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*
D011994:Recombinant Proteins; D013942:Thymine Nucleotides; C112447:dTDP-6-deoxy-4-ketoglucose; C019111:thymidine 3',5'-diphosphate; D013395:Sucrose; D005964:Glucosyltransferases; C022699:sucrose synthase; D006836:Hydro-Lyases; C022771:dTDPglucose 4,6-dehydratase; D005947:Glucose