Studies on the carbodiimide-mediated model couplings of Z-Pro-Leu-OH with benzoaza-15-crown-5

Int J Pept Protein Res. 1993 Jul;42(1):20-3. doi: 10.1111/j.1399-3011.1993.tb00344.x.

Abstract

A series of model DCC-mediated couplings of Z-Pro-D-Leu-OH with 2,3-benzo-10-aza-1,4,7,13-tetraoxacyclopentadeca-2-ene were studied by high-performance liquid chromatography. It was found that racemization during preparation of N-(Z-Pro-Leu-)benzoaza-15-crown-5 is promoted by HOBT, an additive usually reducing this process.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Crown Ethers*
  • Dicyclohexylcarbodiimide
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry*
  • Ethers, Cyclic / chemical synthesis
  • Ethers, Cyclic / chemistry*
  • Models, Chemical
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry
  • Stereoisomerism
  • Triazoles

Substances

  • Crown Ethers
  • Dipeptides
  • Ethers, Cyclic
  • Oligopeptides
  • Triazoles
  • 15-crown-5
  • Dicyclohexylcarbodiimide
  • prolylleucine
  • 1-hydroxybenzotriazole