Synthesis of naturally occurring uridine-alpha-amino acid derivatives by the application of Ugi reaction

Nucleic Acids Symp Ser. 1980:(8):s49-52.

Abstract

A simultaneous condensation (Ugi reaction) of four components (aldehyde, amine, isocyanide, and carboxylic acid) may be a useful reaction for the construction of N,N'-disubstituted alpha-aminocarboxamide structure. We have found that the reaction involving (2-picolyl 1-oxide) amine (op-amine) gave rise to a product, one of whose nitrogen-substituent could be easily removed to give mono-substituted derivative. Thus, the polyoxin skeleton as well as 3-(3-amino-3-carboxypropyl) uridine (a modified nucleoside in certain t-RNAs) were synthesized by the Ugi reaction by the use of the "op"-amine and appropriate aldehyde derived from uridine. Attempted synthesis of these nucleoside derivatives by the condensation involving (2-picolyl 1-oxide) isocyanide as well as the "op"-amine will be also touched on briefly.

MeSH terms

  • Indicators and Reagents
  • Methods
  • Peptides / chemical synthesis
  • Pyrimidine Nucleosides / chemical synthesis
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis

Substances

  • Indicators and Reagents
  • Peptides
  • Pyrimidine Nucleosides
  • polyoxin
  • 3-(3-amino-3-carboxypropyl)uridine
  • Uridine