Lipophilic sugar nucleotide synthesis by structure-based design of nucleotidylyltransferase substrates

Org Biomol Chem. 2008 Feb 7;6(3):477-84. doi: 10.1039/b716955h. Epub 2007 Dec 11.

Abstract

Structure-based design of alkyl sugar-1-phosphates provides an efficient nucleotidylyltransferase-catalyzed synthesis of a series of new lipophilic sugar nucleotides possessing long or branched alkyl chains, thereby demonstrating the utility of nucleotidylyltransferases to catalyze the synthesis of sugar nucleotides with potential applications in lipopolysaccharide and lipoglycopeptide biosynthesis.

MeSH terms

  • Binding Sites
  • Crystallography, X-Ray
  • Glucose / analogs & derivatives
  • Glucose / chemistry
  • Glucose / metabolism
  • Models, Molecular
  • Nucleotides / chemical synthesis*
  • Nucleotidyltransferases / chemistry
  • Nucleotidyltransferases / metabolism*
  • Protein Structure, Secondary
  • Pseudomonas aeruginosa / enzymology*
  • Rhamnose / analogs & derivatives
  • Rhamnose / chemistry
  • Rhamnose / metabolism
  • Substrate Specificity
  • Sugar Phosphates
  • Thymine Nucleotides / chemistry
  • Thymine Nucleotides / metabolism

Substances

  • Nucleotides
  • Sugar Phosphates
  • Thymine Nucleotides
  • deoxythymidine diphosphate-glucose
  • Nucleotidyltransferases
  • Glucose
  • Rhamnose