Synthesis of bromoindolyl 4,7-di-O-methyl-Neu5Ac: specificity toward influenza A and B viruses

Carbohydr Res. 1999 Apr 30;317(1-4):198-203. doi: 10.1016/s0008-6215(99)00058-0.

Abstract

N-Acetylneuraminic acid (Neu5Ac) was converted into the methyl ester methyl ketoside-8,9-epoxy derivative (8). Methylation of 8 followed by deprotection gave 4,7-di-O-methyl-Neu5Ac (10). Compound 10 was converted into the corresponding methyl ester-chloroacetate derivative, which was subsequently coupled to 5-bromo-indol-3-ol to give the chromogenic product (13). Deprotection of 13 gave 5-bromo-indol-3-yl 4,7-di-O-methyl-Neu5Ac (5). The product 5 was specifically cleaved by sialidase from either influenza A or influenza B virus to give an indigo-blue precipitate, but was not cleaved by several bacterial or viral sialidases tested. The properties of product 5 relative to a fluorescent substrate for sialidase were also documented.

MeSH terms

  • Arthrobacter / enzymology
  • Carbohydrate Conformation
  • Clostridium perfringens / enzymology
  • Humans
  • Influenza A virus / enzymology*
  • Influenza A virus / isolation & purification
  • Influenza B virus / enzymology*
  • Influenza B virus / isolation & purification
  • Influenza, Human / diagnosis
  • Molecular Structure
  • N-Acetylneuraminic Acid / analogs & derivatives*
  • N-Acetylneuraminic Acid / chemical synthesis
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / metabolism
  • Neuraminidase / metabolism*
  • Salmonella typhimurium / enzymology
  • Streptococcus / enzymology
  • Substrate Specificity

Substances

  • 5-bromoindolyl-4,7-di-O-methyl-N-acetylneuraminic acid
  • Neuraminidase
  • N-Acetylneuraminic Acid