A new route to dTDP-6-deoxy-l-talose and dTDP-L-rhamnose: dTDP-L-rhamnose 4-epimerase in Burkholderia thailandensis

Bioorg Med Chem Lett. 2011 Jul 1;21(13):3914-7. doi: 10.1016/j.bmcl.2011.05.030. Epub 2011 May 15.

Abstract

dTDP-L-rhamnose (dTDP-Rha)-synthesizing dTDP-6-deoxy-L-lyxo-4-hexulose reductase (4-KR) and dTDP-Rha 4-epimerase were characterized from Burkholderia thailandensis E264 by utilizing rmlD(Bth) (BTH_I1472) and wbiB(Bth) (BTH_I1476), respectively. Incubation of the recombinant WbiB(Bth) with RmlA/RmlB/RmlC/Tal, which has previously been shown to generate dTDP-6-deoxy-L-talose (dTDP-6dTal) from α-D-glucose-1-phosphate, dTTP, and NADPH, produced dTDP-Rha. (1)H NMR measurements confirmed that both RmlA/RmlB/RmlC/Tal/WbiB(Bth) and RmlA/RmlB/RmlC/RmlD produced dTDP-Rha. WbiB(Bth) alone produced dTDP-Rha when incubated with dTDP-6dTal. This is the first report to demonstrate epimerase activity interconverting between dTDP-Rha and dTDP-6dTal.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Burkholderia / enzymology*
  • Burkholderia / genetics
  • Carbohydrate Epimerases / chemistry*
  • Chromatography, High Pressure Liquid
  • Deoxy Sugars / chemistry*
  • Hexoses / chemistry*
  • Molecular Structure
  • Nucleoside Diphosphate Sugars / chemistry*
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Thymine Nucleotides / chemistry*

Substances

  • Deoxy Sugars
  • Hexoses
  • Nucleoside Diphosphate Sugars
  • Recombinant Proteins
  • Thymine Nucleotides
  • thymidine diphosphate rhamnose
  • 6-deoxytalose
  • Carbohydrate Epimerases