Eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group for the synthesis of Cys-containing peptides

Chemistry. 2012 Dec 7;18(50):16166-76. doi: 10.1002/chem.201201370. Epub 2012 Oct 18.

Abstract

Enzyme-labile protecting groups have emerged as a green alternative to conventional protecting groups. These groups introduce a further orthogonal dimension and eco-friendliness into protection schemes for the synthesis of complex polyfunctional organic molecules. S-Phacm, a Cys-protecting group, can be easily removed by the action of a covalently immobilized PGA enzyme under very mild conditions. Herein, the versatility and reliability of an eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group has been evaluated for the synthesis of diverse Cys-containing peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cysteine / chemistry*
  • Enzymes, Immobilized / chemical synthesis*
  • Enzymes, Immobilized / chemistry*
  • Escherichia coli / chemistry*
  • Green Chemistry Technology
  • Molecular Structure
  • Penicillin Amidase / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry*

Substances

  • Enzymes, Immobilized
  • Peptides
  • Penicillin Amidase
  • Cysteine