One-pot protection-glycosylation reactions for synthesis of lipid II analogues

Chemistry. 2014 Apr 14;20(16):4554-8. doi: 10.1002/chem.201400307. Epub 2014 Mar 12.

Abstract

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II N(ε)-dansylthiourea are significantly improved by using the described methods.

Keywords: biosynthesis; lipid II; one-pot synthesis; peptidoglycans; transglycosylase (TGase).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemistry
  • Chloroacetates / chemistry
  • Disaccharides / chemistry
  • Glycosylation
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry
  • Methyl Ethers / chemical synthesis*
  • Methyl Ethers / chemistry
  • Peptidoglycan Glycosyltransferase / chemistry
  • Peptidoglycan Glycosyltransferase / metabolism
  • Polymers / chemistry
  • Uridine Diphosphate N-Acetylmuramic Acid / analogs & derivatives*
  • Uridine Diphosphate N-Acetylmuramic Acid / chemical synthesis
  • Uridine Diphosphate N-Acetylmuramic Acid / chemistry

Substances

  • (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl ether
  • Acetamides
  • Chloroacetates
  • Disaccharides
  • Hydrocarbons, Chlorinated
  • Methyl Ethers
  • Polymers
  • Uridine Diphosphate N-Acetylmuramic Acid
  • muramyl-NAc-(pentapeptide)pyrophosphoryl-undecaprenol
  • Peptidoglycan Glycosyltransferase
  • trichloroacetamide